Hee Jin Han, Anamika Yadav, Taehun Kim, Jae Eun Lee, Yong Ho Lee. “Catalytic S-to-CC transmutation of benzothiazoles into quinolines.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007825/v1

Crude reaction mixture
GC–MS n-Dodecane: RT = 8.941 min; peak at RT = 14.36 min: molecular ion at m/z 256, assigned to S₈; M+2 peak at m/z 258 with a relative intensity of approximately one-third of the molecular ion at m/z 256; image data were not transcribed
GC–FID No corresponding peak was observed at RT = 14.36 min
SI, pp. S24–S25
Authentic elemental sulfur (S₈)
GC–MS, identical conditions RT = 14.36 min; m/z 256
GC–FID, identical conditions No peak was observed
SI, p. S24
Solid residue isolated from the reaction mixture
XPS calibration Binding energies were calibrated against the C 1s peak of adventitious carbon at 284.6 eV; image data were not transcribed
XPS, Ni2p3 Start BE: 866.58; Peak BE: 853.2; End BE: 847.78; Height: 37669.89 CPS; FWHM: 1.51 eV; Area (P): 107155.1 CPS.eV; Atomic %: 22.05; SF: 14.61
XPS, S2p Start BE: 173.28; Peak BE: 162.43; End BE: 158.68; Height: 18338.36 CPS; FWHM: 2.49 eV; Area (P): 67377.28 CPS.eV; Atomic %: 77.95; SF: 1.67
TEM and STEM–EDS (115 kx, 200 kV) The nickel and sulfur signals are co-localized throughout the aggregated particles, consistent with the formation of a nickel sulfide species (NiₓSᵧ) during the reaction; image data were not transcribed
SI, pp. S28–S29
Parallel kinetic isotope effect experiments
¹H NMR reporting basis 1,3,5-Trimethoxybenzene internal standard; yields based on the limiting reagent; mean and standard deviation values from 12 independent reactions per substrate for each time point
¹H NMR, 15 s 3b yield: 34.0 ± 7.3 %; 3b-d yield: 50.0 ± 5.6 %; 3b-d: 93 ± 1.7 %[D] at C2
¹H NMR, 30 s 3b yield: 51.0 ± 7.5 %; 3b-d yield: 64.0 ± 5.3 %; 3b-d: 92 ± 2.0 %[D] at C2
¹H NMR, 60 s 3b yield: 62.0 ± 5.2 %; 3b-d yield: 73.0 ± 4.1 %; 3b-d: 92 ± 1.5 %[D] at C2
SI, pp. S33–S34
Large-scale experiment and kinetic profiling
GC reporting basis n-Dodecane internal standard; yields based on the limiting reagent; 1a and 2b yields correspond to unreacted starting material; 3b:3′b ratio determined by GC area percentage; 6′b denotes the minor regioisomer of 6b; 4b and 5b were not detected in any entry
GC, 5 min 1a yield: 32 %; 2b yield: 39 %; 3b yield: 64 %; 3b:3′b: >20:1; 6b+6′b yield: 9 %; 7a yield: 9 %
GC, 10 min 1a yield: 33 %; 2b yield: 40 %; 3b yield: 66 %; 3b:3′b: >20:1; 6b+6′b yield: 10 %; 7a yield: 10 %
GC, 1 h 1a yield: 33 %; 2b yield: 42 %; 3b yield: 66 %; 3b:3′b: >20:1; 6b+6′b yield: 9 %; 7a yield: 9 %
GC, 6 h 1a yield: 34 %; 2b yield: 40 %; 3b yield: 66 %; 3b:3′b: >20:1; 6b+6′b yield: 9 %; 7a yield: 9 %
GC, 24 h 1a yield: 33 %; 2b yield: 42 %; 3b yield: 65 %; 3b:3′b: >20:1; 6b+6′b yield: 9 %; 7a yield: 9 %
GC, 72 h 1a yield: 33 %; 2b yield: 39 %; 3b yield: 64 %; 3b:3′b: >20:1; 6b+6′b yield: 9 %; 7a yield: 10 %
SI, p. S36
3-Butyl-4-phenylquinoline (3b)
¹H NMR (500 MHz, CDCl₃) δ 8.88 (s, 1H), 8.11 (d, J = 8.5 Hz, 1H), 7.63 (ddd, J = 8.4, 5.7, 2.5 Hz, 1H), 7.57 – 7.49 (m, 2H), 7.49 – 7.43 (m, 1H), 7.39 (d, J = 6.4 Hz, 2H), 7.30 – 7.24 (m, 2H), 2.59 (t, J = 7.9 Hz, 2H), 1.50 (tt, J = 7.8, 6.6 Hz, 2H), 1.28 – 1.20 (m, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.51, 146.78, 146.11, 136.74, 132.97, 129.59, 129.38, 128.51, 128.36, 127.98, 127.91, 126.49, 126.29, 33.69, 30.84, 22.58, 13.87; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₀N 262.1596, found 262.1590
SI, pp. S38, S120–S122
3-Butyl-6-methyl-4-phenylquinoline (3c)
¹H NMR (500 MHz, CDCl₃) δ 8.79 (s, 1H), 8.00 (d, J = 8.5 Hz, 1H), 7.54 – 7.44 (m, 4H), 7.27 (d, J = 1.6 Hz, 1H), 7.25 (t, J = 1.4 Hz, 1H), 7.13 (s, 1H), 2.57 – 2.52 (m, 2H), 2.38 (s, 3H), 1.52 – 1.44 (m, 2H), 1.26 – 1.19 (m, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.64, 145.46, 145.39, 136.95, 136.32, 132.92, 130.56, 129.62, 129.17, 128.49, 127.86, 127.82, 125.04, 33.68, 30.85, 22.57, 21.90, 13.86; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂N 276.1752, found 276.1751
SI, pp. S39, S123
3-Butyl-6-methoxy-4-phenylquinoline (3d)
¹H NMR (500 MHz, CDCl₃) δ 8.73 (s, 1H), 8.03 (d, J = 9.1 Hz, 1H), 7.55 – 7.44 (m, 3H), 7.33 – 7.23 (m, 3H), 6.69 – 6.62 (m, 1H), 3.67 (s, 3H), 2.59 – 2.50 (m, 2H), 1.53 – 1.43 (m, 2H), 1.27 – 1.18 (m, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 157.87, 149.68, 145.24, 142.63, 136.90, 130.67, 129.45, 128.64, 128.00, 120.67, 104.56, 55.41, 33.62, 30.92, 22.56, 13.84; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂NO 292.1701, found 292.1697
SI, pp. S39, S124
3-Butyl-4-phenyl-6-((triethylsilyl)oxy)quinoline (3e)
¹H NMR (500 MHz, CDCl₃) δ 8.71 (s, 1H), 7.97 (d, J = 9.0 Hz, 1H), 7.53 – 7.43 (m, 3H), 7.26 – 7.20 (m, 3H), 6.69 (d, J = 2.6 Hz, 1H), 2.60 – 2.54 (m, 2H), 1.53 – 1.45 (m, 2H), 1.24 (h, J = 7.4 Hz, 2H), 0.89 (t, J = 7.9 Hz, 9H), 0.79 (t, J = 7.4 Hz, 3H), 0.62 (q, J = 7.9 Hz, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.86, 150.38, 144.78, 142.97, 137.00, 132.86, 130.73, 129.52, 129.06, 128.49, 127.86, 124.07, 112.77, 33.67, 30.88, 22.58, 13.87, 6.63, 5.02; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₃₄NOSi 392.2409, found 392.2407
SI, pp. S39–S40, S125
3-Butyl-4-phenylquinolin-6-amine (3f)
¹H NMR (500 MHz, CDCl₃) δ 8.60 (s, 1H), 7.89 (d, J = 8.8 Hz, 1H), 7.52 – 7.41 (m, 3H), 7.25 – 7.20 (m, 2H), 7.04 (d, J = 8.8 Hz, 1H), 6.43 (s, 1H), 3.80 (s, 2H), 2.53 – 2.46 (m, 2H), 1.50 – 1.41 (m, 2H), 1.21 (h, J = 7.4 Hz, 2H), 0.77 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 148.91, 144.63, 143.75, 142.01, 137.28, 133.05, 130.54, 129.62, 129.25, 128.45, 127.66, 120.23, 106.48, 33.59, 30.85, 22.54, 13.83; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₁N₂ 277.1704, found 277.1701
SI, pp. S40, S126
3-Butyl-6-fluoro-4-phenylquinoline (3g)
¹H NMR (500 MHz, CDCl₃) δ 8.82 (s, 1H), 8.09 (dd, J = 9.2, 5.5 Hz, 1H), 7.56 – 7.45 (m, 3H), 7.38 (ddd, J = 9.2, 8.0, 2.8 Hz, 1H), 7.26 – 7.21 (m, 2H), 6.99 (dd, J = 10.3, 2.8 Hz, 1H), 2.60 – 2.54 (m, 2H), 1.49 (dtd, J = 9.9, 7.6, 6.0 Hz, 2H), 1.23 (dq, J = 14.7, 7.4 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 160.65 (d, J = 245 Hz), 151.85, 145.59, 143.95, 136.25, 133.69, 131.82 (d, J = 10 Hz), 129.43, 128.83 (d, J = 10 Hz), 128.70, 128.22, 118.44 (d, J = 25 Hz), 109.60 (d, J = 25 Hz), 33.56, 30.85, 22.55, 13.81; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −112.98; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉FN 280.1501, found 280.1498
SI, pp. S40, S127–S128
3-Butyl-6-chloro-4-phenylquinoline (3h)
¹H NMR (500 MHz, CDCl₃) δ 8.84 (s, 1H), 8.03 (d, J = 8.9 Hz, 1H), 7.57 – 7.45 (m, 4H), 7.35 (d, J = 2.3 Hz, 1H), 7.26 – 7.22 (m, 2H), 2.60 – 2.52 (m, 2H), 1.48 (dtd, J = 9.9, 7.6, 6.0 Hz, 2H), 1.23 (h, J = 7.3 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.72, 145.29, 145.24, 135.99, 133.94, 132.41, 131.06, 129.48, 129.25, 128.72, 128.69, 128.29, 125.06, 33.54, 30.85, 22.55, 13.81; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉ClN 296.1206, found 296.1200
SI, pp. S40–S41, S129
3-Butyl-4-phenyl-6-(trifluoromethyl)quinoline (3i)
¹H NMR (500 MHz, CDCl₃) δ 8.96 (s, 1H), 8.22 (d, J = 8.8 Hz, 1H), 7.80 (dd, J = 8.8, 2.0 Hz, 1H), 7.71 (s, 1H), 7.58 – 7.49 (m, 3H), 7.29 – 7.23 (m, 2H), 2.64 – 2.58 (m, 2H), 1.50 (dtd, J = 9.9, 7.6, 6.0 Hz, 2H), 1.27 – 1.21 (m, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR δ 154.61, 147.81, 146.99, 135.61, 134.43, 130.69, 129.47, 128.82, 128.55, 128.40 (q, J = 31.5 Hz), 127.13, 124.22 (q, J = 4.6 Hz), 124.21 (q, J = 273.4 Hz), 124.08 (q, J = 2.9 Hz), 33.56, 30.88, 22.57, 13.81; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −62.22; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₁₉F₃N 330.1469, found 330.1469
SI, pp. S41, S130–S131
3-Butyl-4-phenyl-6-(trifluoromethoxy)quinoline (3j)
¹H NMR (500 MHz, CDCl₃) δ 8.88 (s, 1H), 8.14 (d, J = 9.1 Hz, 1H), 7.56 – 7.47 (m, 4H), 7.27 – 7.24 (m, 2H), 7.22 – 7.19 (m, 1H), 2.62 – 2.57 (m, 2H), 1.53 – 1.46 (m, 2H), 1.24 (h, J = 7.4 Hz, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.05, 147.13, 146.02, 145.14, 135.89, 134.07, 131.61, 129.44, 128.77, 128.41, 122.27, 120.60 (q, J = 258.3 Hz), 117.03, 33.56, 30.88, 22.57, 13.81; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −57.79; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₁₉F₃NO 346.1418, found 346.1411
SI, pp. S41, S132–S133
3-Butyl-4-phenylquinoline-6-carbonitrile (3k)
¹H NMR (500 MHz, CDCl₃) δ 8.98 (s, 1H), 8.18 (d, J = 8.6 Hz, 1H), 7.81 – 7.75 (m, 2H), 7.59 – 7.52 (m, 3H), 7.26 – 7.22 (m, 2H), 2.64 – 2.58 (m, 2H), 1.54 – 1.47 (m, 2H), 1.24 (dt, J = 14.7, 7.4 Hz, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 155.39, 147.74, 146.53, 135.12, 134.96, 132.94, 130.95, 129.39, 129.06, 128.95, 128.78, 127.60, 119.06, 110.16, 33.51, 30.86, 22.56, 13.81; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₁₉N₂ 287.1548, found 287.1545
SI, pp. S41–S42, S134
Ethyl 3-butyl-4-phenylquinoline-6-carboxylate (3l)
¹H NMR (500 MHz, CDCl₃) δ 8.93 (s, 1H), 8.24 – 8.11 (m, 3H), 7.56 – 7.47 (m, 3H), 7.28 – 7.25 (m, 2H), 4.33 (q, J = 7.1 Hz, 2H), 2.62 – 2.57 (m, 2H), 1.53 – 1.46 (m, 2H), 1.33 (t, J = 7.1 Hz, 3H), 1.24 (h, J = 7.4 Hz, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 166.45, 154.55, 148.70, 147.40, 135.90, 133.86, 129.71, 129.56, 129.45, 128.66, 128.43, 128.35, 127.88, 127.22, 61.26, 33.58, 30.84, 22.56, 14.36, 13.81; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₂H₂₄NO₂ 334.1807, found 334.1800
SI, pp. S42, S135
Benzyl 3-butyl-4-phenylquinoline-6-carboxylate (3m)
¹H NMR (500 MHz, CDCl₃) δ 8.94 (s, 1H), 8.26 – 8.23 (m, 2H), 8.14 (d, J = 9.2 Hz, 1H), 7.57 – 7.50 (m, 3H), 7.36 (m, 5H), 7.29 – 7.26 (m, 2H), 5.33 (s, 2H), 2.65 – 2.59 (m, 2H), 1.55 – 1.47 (m, 2H), 1.29 – 1.21 (m, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 166.20, 154.71, 148.76, 147.45, 136.14, 135.87, 133.91, 129.87, 129.79, 129.60, 128.69, 128.68, 128.37, 128.26, 128.04, 127.88, 127.28, 66.81, 33.59, 30.85, 22.58, 13.83; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₇H₂₆NO₂ 396.1963, found 396.1954
SI, pp. S42–S43, S136
(3-Butyl-4-phenylquinolin-6-yl)(piperidin-1-yl)methanone (3n)
¹H NMR (500 MHz, CDCl₃) δ 8.89 (s, 1H), 8.12 (d, J = 8.6 Hz, 1H), 7.64 (dd, J = 8.6, 1.7 Hz, 1H), 7.56 – 7.39 (m, 4H), 7.26 – 7.20 (m, 2H), 3.65 (s, 2H), 3.25 (s, 2H), 2.66 – 2.48 (m, 2H), 1.62 (s, 4H), 1.52 – 1.45 (m, 2H), 1.38 (s, 2H), 1.22 (dt, J = 14.7, 7.3 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 169.85, 153.35, 146.44, 136.12, 134.33, 129.83, 129.48, 128.63, 128.20, 126.87, 125.15, 125.01, 123.64, 121.02, 48.88, 43.21, 33.59, 30.84, 26.48, 25.64, 24.65, 22.53, 13.82; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₂₉N₂O 373.2279, found 373.2277
SI, pp. S43, S137
3-Butyl-7-methoxy-4-phenylquinoline (3o)
¹H NMR (500 MHz, CDCl₃) δ 8.79 (s, 1H), 7.53 – 7.43 (m, 4H), 7.31 – 7.23 (m, 3H), 7.04 (dd, J = 9.2, 2.5 Hz, 1H), 3.94 (s, 3H), 2.59 – 2.50 (m, 2H), 1.47 (dtd, J = 9.7, 7.6, 6.1 Hz, 2H), 1.25 – 1.18 (m, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.84, 152.60, 148.48, 146.12, 136.89, 130.92, 129.52, 128.44, 127.89, 127.38, 122.97, 119.34, 107.42, 55.59, 33.78, 30.59, 22.52, 13.85; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂NO 292.1701, found 292.1700
SI, pp. S43, S138
3-Butyl-7-fluoro-4-phenylquinoline (3p)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 7.73 (dd, J = 10.0, 2.6 Hz, 1H), 7.55 – 7.45 (m, 3H), 7.38 (dd, J = 9.2, 6.1 Hz, 1H), 7.26 – 7.23 (m, 2H), 7.16 (ddd, J = 9.2, 8.2, 2.6 Hz, 1H), 2.60 – 2.53 (m, 2H), 1.48 (dtd, J = 9.8, 7.6, 6.0 Hz, 2H), 1.27 – 1.19 (m, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.43 (d, J = 249.48 Hz), 153.57, 147.78 (d, J = 12.6 Hz), 146.24, 136.47, 132.41, 129.48, 128.60, 128.49 (d, J = 9.6 Hz), 128.17, 125.02, 116.71 (d, J = 25.2 Hz), 112.90 (d, J = 20.16 Hz), 33.66, 30.69, 22.54, 13.82; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −112.13; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉FN 280.1501, found 280.1494
SI, pp. S43–S44, S139–S140
3-Butyl-7-chloro-4-phenylquinoline (3q)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.09 (dd, J = 1.7, 0.6 Hz, 1H), 7.54 – 7.44 (m, 3H), 7.31 (dd, J = 2.2, 1.3 Hz, 2H), 7.26 – 7.21 (m, 2H), 2.60 – 2.53 (m, 2H), 1.48 (dtd, J = 9.8, 7.6, 6.0 Hz, 2H), 1.23 (h, J = 7.3 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.52, 147.25, 146.07, 136.22, 134.22, 133.25, 129.47, 128.61, 128.31, 128.19, 127.67, 127.37, 126.35, 33.55, 30.75, 22.53, 13.80; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉ClN 296.1206, found 296.1200
SI, pp. S44, S141
7-Bromo-3-butyl-4-phenylquinoline (3r)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.28 (d, J = 2.0 Hz, 1H), 7.55 – 7.47 (m, 3H), 7.45 (dd, J = 9.0, 2.0 Hz, 1H), 7.27 – 7.23 (m, 3H), 2.59 – 2.53 (m, 2H), 1.49 (dtd, J = 9.9, 7.6, 6.0 Hz, 2H), 1.23 (dq, J = 14.6, 7.3 Hz, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.50, 147.55, 146.19, 136.20, 133.45, 131.68, 129.93, 129.51, 128.66, 128.24, 127.79, 126.67, 122.48, 33.55, 30.83, 22.56, 13.83; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉BrN 340.0700, found 340.0694
SI, pp. S44, S142
3-Butyl-8-methyl-4-phenylquinoline (3s)
¹H NMR (500 MHz, CDCl₃) δ 8.91 (s, 1H), 7.54 – 7.45 (m, 4H), 7.30 – 7.23 (m, 4H), 2.87 (s, 3H), 2.62 – 2.56 (m, 2H), 1.55 – 1.47 (m, 2H), 1.29 – 1.22 (m, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.24, 146.29, 145.89, 137.17, 136.91, 132.56, 129.60, 128.61, 128.41, 127.82, 127.80, 126.13, 124.39, 33.61, 30.79, 22.50, 18.47, 13.85; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂N 276.1752, found 276.1750
SI, pp. S44–S45, S143
3-Butyl-8-methoxy-4-phenylquinoline (3t)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 7.52 – 7.43 (m, 3H), 7.30 – 7.26 (m, 1H), 7.26 – 7.22 (m, 2H), 6.99 – 6.95 (m, 1H), 6.93 (dd, J = 8.5, 1.0 Hz, 1H), 4.09 (s, 3H), 2.59 – 2.53 (m, 2H), 1.47 (tt, J = 7.8, 6.1 Hz, 2H), 1.25 – 1.18 (m, 2H), 0.77 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 155.54, 151.19, 145.96, 138.77, 137.01, 133.53, 129.53, 128.95, 128.41, 127.86, 126.38, 118.12, 106.52, 56.10, 33.54, 30.78, 22.47, 13.80; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂NO 292.1701, found 292.1701
SI, pp. S45, S144
8-(Benzyloxy)-3-butyl-4-phenylquinoline (3u)
¹H NMR (500 MHz, CDCl₃) δ 8.93 (s, 1H), 7.53 (d, J = 7.1 Hz, 2H), 7.51 – 7.42 (m, 3H), 7.36 (t, J = 7.5 Hz, 2H), 7.29 (d, J = 7.3 Hz, 1H), 7.26 – 7.23 (m, 2H), 7.20 – 7.16 (m, 1H), 6.96 – 6.91 (m, 2H), 5.46 (s, 2H), 2.61 – 2.55 (m, 2H), 1.53 – 1.46 (m, 2H), 1.25 – 1.21 (m, 2H), 0.79 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.39, 151.28, 145.88, 139.01, 137.21, 136.97, 133.38, 129.47, 129.05, 128.65, 128.36, 127.80, 127.77, 127.11, 126.20, 118.36, 108.85, 70.77, 33.51, 30.74, 22.44, 13.78; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₆H₂₆NO 368.2014, found 368.2010
SI, pp. S45–S46, S145
3-Butyl-8-chloro-4-phenylquinoline (3v)
¹H NMR (500 MHz, CDCl₃) δ 8.98 (s, 1H), 7.74 (dd, J = 7.1, 1.6 Hz, 1H), 7.54 – 7.46 (m, 3H), 7.33 – 7.27 (m, 2H), 7.24 (dt, J = 5.7, 1.5 Hz, 2H), 2.61 – 2.56 (m, 2H), 1.52 – 1.45 (m, 2H), 1.26 – 1.20 (m, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.00, 146.60, 143.10, 136.39, 133.97, 133.58, 129.49, 129.38, 128.59, 128.50, 128.21, 126.22, 125.54, 33.47, 30.79, 22.48, 13.80; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉ClN 296.1206, found 296.1201
SI, pp. S46, S146
3-Butyl-4-phenylquinolin-5-amine (3w)
¹H NMR (500 MHz, CDCl₃) δ 8.74 (s, 1H), 7.54 (dd, J = 8.3, 1.2 Hz, 1H), 7.53 – 7.47 (m, 3H), 7.42 – 7.38 (m, 1H), 7.37 – 7.33 (m, 2H), 6.58 (dd, J = 7.5, 1.2 Hz, 1H), 3.58 (s, 2H), 2.42 – 2.34 (m, 2H), 1.46 – 1.39 (m, 2H), 1.23 – 1.17 (m, 2H), 0.77 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.89, 148.77, 144.01, 139.52, 132.46, 129.15, 128.94, 128.72, 128.42, 120.29, 116.24, 111.73, 33.88, 30.57, 22.66, 13.83; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₁N₂ 277.1705, found 277.1701
SI, pp. S46, S147
3-Butyl-6,7-dimethyl-4-phenylquinoline (3x)
¹H NMR (500 MHz, CDCl₃) δ 8.76 (s, 1H), 7.86 (s, 1H), 7.54 – 7.45 (m, 3H), 7.28 – 7.23 (m, 2H), 7.10 (s, 1H), 2.57 – 2.51 (m, 2H), 2.44 (s, 3H), 2.29 (s, 3H), 1.52 – 1.43 (m, 2H), 1.23 (dt, J = 14.8, 7.4 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.61, 146.05, 145.15, 138.38, 137.14, 136.30, 132.06, 129.63, 128.87, 128.44, 127.79, 126.36, 125.43, 33.72, 30.79, 22.55, 20.29, 20.26, 13.85; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₂₄N 290.1908, found 290.1904
SI, pp. S46–S47, S148–S150
3-Butyl-5,8-dimethyl-4-phenylquinoline (3y)
¹H NMR (500 MHz, CDCl₃) δ 8.84 (s, 1H), 7.43 (dd, J = 6.2, 2.7 Hz, 3H), 7.37 (d, J = 7.2 Hz, 1H), 7.25 – 7.21 (m, 2H), 7.10 (d, J = 7.2 Hz, 1H), 2.81 (s, 3H), 2.46 – 2.41 (m, 2H), 1.84 (s, 3H), 1.48 – 1.40 (m, 2H), 1.21 (h, J = 7.4 Hz, 2H), 0.77 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.26, 147.03, 146.25, 140.77, 135.69, 133.73, 133.48, 129.89, 129.67, 128.41, 127.95, 127.63, 126.42, 33.82, 30.87, 24.53, 22.66, 19.03, 13.85; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₂₄N 290.1908, found 290.1907
SI, pp. S47, S151
3-Butyl-6,8-dichloro-4-phenylquinoline (3z)
¹H NMR (500 MHz, CDCl₃) δ 8.95 (s, 1H), 7.73 (d, J = 2.2 Hz, 1H), 7.57 – 7.47 (m, 3H), 7.28 (d, J = 2.2 Hz, 1H), 7.24 – 7.20 (m, 2H), 2.60 – 2.55 (m, 2H), 1.51 – 1.44 (m, 2H), 1.26 – 1.18 (m, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.10, 145.90, 135.64, 135.05, 134.77, 131.67, 129.67, 129.41, 129.11, 128.82, 128.54, 124.39, 33.37, 30.85, 22.48, 13.78; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₈Cl₂N 330.0816, found 330.0812
SI, pp. S47, S152
3-Butyl-4-phenyl-1,8-naphthyridine (3aa)
¹H NMR (500 MHz, CDCl₃) δ 9.06 (s, 1H), 9.03 – 8.98 (m, 1H), 7.78 (dd, J = 8.3, 1.6 Hz, 1H), 7.55 – 7.46 (m, 3H), 7.32 (dd, J = 8.3, 4.1 Hz, 1H), 7.26 – 7.21 (m, 2H), 2.65 – 2.56 (m, 2H), 1.53 – 1.45 (m, 2H), 1.23 (h, J = 7.4 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 155.62, 154.91, 152.31, 147.13, 135.60, 134.10, 129.52, 128.67, 128.38, 122.48, 121.93, 33.49, 30.63, 22.51, 13.79; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₈H₁₉N₂ 263.1548, found 263.1544
SI, pp. S47–S48, S153
3-Butyl-4-phenyl-1,7-naphthyridine (3ab)
¹H NMR (500 MHz, CDCl₃) δ 9.47 (s, 1H), 8.93 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 7.55 – 7.45 (m, 3H), 7.25 – 7.22 (m, 2H), 7.20 (d, J = 5.3 Hz, 1H), 2.66 – 2.58 (m, 2H), 1.53 – 1.45 (m, 2H), 1.22 (h, J = 7.4 Hz, 2H), 0.77 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.05, 153.93, 144.84, 143.94, 141.93, 137.18, 135.04, 131.08, 129.39, 128.74, 128.47, 118.39, 33.35, 30.96, 22.51, 13.74; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₈H₁₉N₂ 263.1548, found 263.1545
SI, pp. S48, S154
3-Butyl-4-phenyl-2-(trifluoromethyl)quinoline (3ac)
¹H NMR (500 MHz, CDCl₃) δ 8.21 (d, J = 8.4 Hz, 1H), 7.71 (ddd, J = 8.4, 6.8, 1.4 Hz, 1H), 7.58 – 7.45 (m, 4H), 7.35 – 7.31 (m, 1H), 7.30 – 7.26 (m, 2H), 2.76 – 2.68 (m, 2H), 1.42 – 1.34 (m, 2H), 1.16 (h, J = 7.3 Hz, 2H), 0.69 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.53, 146.6 (q, J = 32.76 Hz), 144.97, 136.27, 131.30, 130.16, 129.57, 129.51, 129.10, 128.65, 128.47, 128.39, 126.27, 122.40 (q, J = 277.2 Hz), 33.40, 28.76 (q, J = 2.52 Hz), 23.06, 13.42; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −63.51; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₁₉F₃N 330.1470, found 330.1466
SI, pp. S48–S49, S155–S158
3-Butyl-4-(4-(tert-butyl)phenyl)quinoline (3ad)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 7.62 (ddd, J = 8.4, 6.7, 1.5 Hz, 1H), 7.54 – 7.48 (m, 2H), 7.45 (dd, J = 8.5, 1.4 Hz, 1H), 7.38 (ddd, J = 8.3, 6.7, 1.1 Hz, 1H), 7.22 – 7.16 (m, 2H), 2.62 – 2.56 (m, 2H), 1.54 – 1.46 (m, 2H), 1.41 (s, 9H), 1.27 – 1.20 (m, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.33, 150.90, 146.64, 146.47, 133.54, 133.17, 129.24, 129.16, 128.32, 128.13, 126.47, 126.39, 125.32, 34.82, 33.64, 31.54, 30.76, 22.49, 13.78; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₃H₂₈N 318.2222, found 318.2218
SI, pp. S50, S159–S161
3-Butyl-4-(4-methoxyphenyl)quinoline (3ae)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.63 (ddd, J = 8.4, 6.6, 1.6 Hz, 1H), 7.45 (dd, J = 8.4, 1.5 Hz, 1H), 7.39 (ddd, J = 8.3, 6.7, 1.3 Hz, 1H), 7.22 – 7.16 (m, 2H), 7.08 – 7.02 (m, 2H), 3.91 (s, 3H), 2.63 – 2.57 (m, 2H), 1.54 – 1.45 (m, 2H), 1.29 – 1.20 (m, 2H), 0.81 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.33, 152.58, 146.87, 145.91, 133.34, 130.78, 129.41, 128.83, 128.29, 126.41, 126.35, 113.96, 55.48, 33.74, 30.91, 22.61, 13.94; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂NO 292.1701, found 292.1696
SI, pp. S51, S162–S164
4-(3-Butylquinolin-4-yl)-N,N-dimethylaniline (3af)
¹H NMR (500 MHz, CDCl₃) δ 8.84 (s, 1H), 8.10 (dd, J = 8.4, 1.2 Hz, 1H), 7.61 (ddd, J = 8.3, 6.8, 1.5 Hz, 1H), 7.54 (dd, J = 8.3, 1.4 Hz, 1H), 7.38 (ddd, J = 8.3, 6.7, 1.2 Hz, 1H), 7.16 – 7.10 (m, 2H), 6.88 – 6.82 (m, 2H), 3.05 (s, 6H), 2.68 – 2.61 (m, 2H), 1.55 – 1.48 (m, 2H), 1.26 (h, J = 7.3 Hz, 2H), 0.82 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.25, 150.11, 147.06, 146.59, 133.48, 130.44, 128.98, 128.67, 128.26, 126.68, 126.26, 124.12, 112.14, 40.59, 33.73, 30.92, 22.59, 13.95; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₂₅N₂ 305.2018, found 305.2011
SI, pp. S51, S165–S166
3-Butyl-4-(4-fluorophenyl)quinoline (3ag)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.15 – 8.06 (m, 1H), 7.64 (ddd, J = 8.4, 6.6, 1.7 Hz, 1H), 7.44 – 7.32 (m, 2H), 7.27 – 7.18 (m, 4H), 2.65 – 2.50 (m, 2H), 1.53 – 1.44 (m, 2H), 1.29 – 1.19 (m, 2H), 0.81 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.56 (d, J = 248.2), 152.53, 146.84, 144.96, 133.22, 132.56 (d, J = 3.78 Hz), 131.30 (d, J = 7.56 Hz), 129.53, 128.45, 127.92, 126.65, 126.00, 115.66 (d, J = 21.42 Hz), 33.70, 30.85, 22.59, 13.88; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −114.01; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉FN 280.1502, found 280.1497
SI, pp. S51–S52, S167–S170
1-(4-(3-Butylquinolin-4-yl)phenyl)ethan-1-one (3ah)
¹H NMR (500 MHz, CDCl₃) δ 8.88 (s, 1H), 8.16 – 8.08 (m, 3H), 7.65 (ddd, J = 8.3, 6.8, 1.5 Hz, 1H), 7.44 – 7.37 (m, 3H), 7.30 (dd, J = 8.5, 1.4 Hz, 1H), 2.71 (s, 3H), 2.60 – 2.52 (m, 2H), 1.54 – 1.44 (m, 2H), 1.23 (m, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 197.79, 152.46, 146.78, 144.86, 141.97, 136.83, 132.71, 130.05, 129.60, 128.61, 128.60, 127.31, 126.84, 125.83, 33.69, 30.89, 26.84, 22.59, 13.88; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₂₂NO 304.1701, found 304.1696
SI, pp. S52, S171–S172
3-Butyl-4-(3-methoxyphenyl)quinoline (3ai)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.11 (d, J = 8.5 Hz, 1H), 7.62 (t, J = 7.7 Hz, 1H), 7.46 – 7.35 (m, 3H), 7.01 (dd, J = 8.4, 2.6 Hz, 1H), 6.85 (d, J = 7.5 Hz, 1H), 6.83 – 6.78 (m, 1H), 3.83 (s, 3H), 2.59 (t, J = 7.9 Hz, 2H), 1.55 – 1.47 (m, 2H), 1.29 – 1.21 (m, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.71, 152.46, 146.76, 145.96, 138.12, 132.86, 129.62, 129.35, 128.37, 127.81, 126.51, 126.32, 122.05, 115.20, 113.55, 55.44, 33.74, 30.85, 22.60, 13.89; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂NO 292.1701, found 292.1698
SI, pp. S52–S53, S173–S175
3-Butyl-4-(naphthalen-2-yl)quinoline (3aj)
¹H NMR (500 MHz, CDCl₃) δ 8.93 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 8.03 – 7.93 (m, 2H), 7.92 – 7.85 (m, 1H), 7.77 (d, J = 1.6 Hz, 1H), 7.64 (ddd, J = 8.3, 6.6, 1.6 Hz, 1H), 7.61 – 7.53 (m, 2H), 7.41 (dd, J = 8.8, 1.6 Hz, 1H), 7.39 – 7.33 (m, 2H), 2.70 – 2.56 (m, 2H), 1.53 (p, J = 7.7 Hz, 2H), 1.29 – 1.17 (m, 2H), 0.77 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.53, 146.79, 145.93, 134.24, 133.23, 133.18, 132.87, 129.43, 128.56, 128.39, 128.20, 128.18, 128.00, 127.65, 126.69, 126.55, 126.54, 126.35, 33.72, 30.91, 22.54, 13.86; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₃H₂₂N 312.1752, found 312.1749
SI, pp. S53, S176–S178
3-Butyl-4-(thiophen-2-yl)quinoline (3ak)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.68 – 7.59 (m, 2H), 7.53 (dd, J = 5.1, 1.2 Hz, 1H), 7.44 (dd, J = 8.4, 6.9 Hz, 1H), 7.22 (dd, J = 5.2, 3.4 Hz, 1H), 7.05 (dd, J = 3.5, 1.2 Hz, 1H), 2.72 – 2.65 (m, 2H), 1.62 – 1.52 (m, 2H), 1.32 (dt, J = 14.8, 7.4 Hz, 2H), 0.85 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.30, 146.72, 138.77, 136.27, 135.27, 129.37, 128.81, 128.64, 128.56, 127.29, 126.87, 126.74, 126.02, 34.00, 31.27, 22.69, 13.94; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₇H₁₈NS 268.1160, found 268.1158
SI, pp. S53–S54, S179–S181
3-Methyl-4-phenylquinoline (3al)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.12 (d, J = 8.4 Hz, 1H), 7.67 – 7.60 (m, 1H), 7.57 – 7.35 (m, 5H), 7.29 – 7.24 (m, 2H), 2.27 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.76, 146.98, 146.39, 136.99, 129.45, 129.35, 128.72, 128.32, 128.17, 128.01, 127.67, 126.55, 126.01, 17.73; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₆H₁₄N 220.1126, found 220.1120
SI, pp. S54, S182–S184
4-(4-Phenylquinolin-3-yl)butan-1-ol (3am)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.63 (dp, J = 8.8, 4.6 Hz, 1H), 7.55 – 7.44 (m, 3H), 7.39 (d, J = 4.1 Hz, 2H), 7.28 – 7.22 (m, 2H), 3.53 (t, J = 6.4 Hz, 2H), 2.65 – 2.58 (m, 2H), 1.88 (bs, 1H), 1.59 (qd, J = 8.6, 6.0 Hz, 2H), 1.53 – 1.44 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.26, 146.78, 146.28, 136.59, 132.49, 129.52, 129.30, 128.58, 128.51, 128.08, 126.59, 126.28, 62.40, 32.44, 30.80, 27.62; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₀NO 278.1545, found 278.1541
SI, pp. S54, S185–S187
3-(4-(Benzyloxy)butyl)-4-phenylquinoline (3an)
¹H NMR (500 MHz, CDCl₃) δ 8.88 (s, 1H), 8.12 (dt, J = 8.4, 1.0 Hz, 1H), 7.68 – 7.60 (m, 1H), 7.54 – 7.43 (m, 3H), 7.41 – 7.38 (m, 2H), 7.35 – 7.30 (m, 2H), 7.30 – 7.25 (m, 5H), 4.42 (s, 2H), 3.36 (t, J = 6.3 Hz, 2H), 2.65 – 2.59 (m, 2H), 1.67 – 1.50 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.40, 146.89, 146.20, 138.68, 136.69, 132.57, 129.57, 129.42, 128.56, 128.46, 128.42, 128.01, 127.88, 127.69, 127.62, 126.52, 126.29, 72.99, 70.00, 30.91, 29.57, 28.13; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₆H₂₆NO 368.2014, found 368.2012
SI, pp. S54–S55, S188–S189
3-(4-Chlorobutyl)-4-phenylquinoline (3ao)
¹H NMR (500 MHz, CDCl₃) δ 8.87 (s, 1H), 8.12 (dt, J = 8.6, 1.0 Hz, 1H), 7.69 – 7.61 (m, 1H), 7.58 – 7.45 (m, 3H), 7.42 – 7.38 (m, 2H), 7.30 – 7.26 (m, 2H), 3.43 – 3.36 (m, 2H), 2.66 – 2.59 (m, 2H), 1.72 – 1.62 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.26, 146.98, 146.36, 136.52, 132.00, 129.52, 129.46, 128.67, 128.60, 128.16, 127.83, 126.65, 126.32, 44.60, 32.21, 30.31, 28.59; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₉ClN 296.1206, found 296.1202
SI, pp. S55, S190–S192
4-(4-Phenylquinolin-3-yl)butanenitrile (3ap)
¹H NMR (500 MHz, CDCl₃) δ 8.86 (s, 1H), 8.13 (d, J = 8.4 Hz, 1H), 7.67 (ddd, J = 8.3, 5.3, 2.9 Hz, 1H), 7.58 – 7.48 (m, 3H), 7.41 (q, J = 4.2 Hz, 2H), 7.27 (d, J = 5.8 Hz, 2H), 2.77 (dd, J = 9.0, 6.8 Hz, 2H), 2.23 (t, J = 7.1 Hz, 2H), 1.84 (p, J = 7.3 Hz, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.69, 147.20, 147.02, 136.08, 130.18, 129.44, 129.33, 129.02, 128.89, 128.47, 127.76, 126.93, 126.34, 119.04, 30.14, 26.88, 16.99; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₇N₂ 273.1392, found 273.1386
SI, pp. S55, S193
4-Phenyl-3-(((triisopropylsilyl)oxy)methyl)quinoline (3ar)
¹H NMR (500 MHz, CDCl₃) δ 9.23 (s, 1H), 8.15 (d, J = 8.3 Hz, 1H), 7.67 (ddd, J = 8.3, 6.7, 1.5 Hz, 1H), 7.54 – 7.46 (m, 4H), 7.42 (ddd, J = 8.3, 6.7, 1.2 Hz, 1H), 7.31 – 7.27 (m, 2H), 4.70 (s, 2H), 1.12 – 1.04 (m, 3H), 1.01 (d, J = 6.5 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.91, 147.66, 145.15, 135.64, 130.96, 129.62, 129.48, 128.90, 128.58, 128.33, 127.20, 126.58, 126.32, 61.88, 18.11, 12.07; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₃₄NOSi 392.2410, found 392.2405
SI, pp. S55–S56, S194
3-Cyclopropyl-4-phenylquinoline (3as, major)
¹H NMR (500 MHz, CDCl₃) δ 8.59 (s, 1H), 8.10 (d, J = 8.4 Hz, 1H), 7.62 (ddd, J = 8.3, 6.6, 1.6 Hz, 1H), 7.57 – 7.50 (m, 2H), 7.50 – 7.43 (m, 2H), 7.42 – 7.33 (m, 3H), 1.79 (ddd, J = 13.8, 8.5, 5.4 Hz, 1H), 0.92 – 0.81 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 148.12, 146.74, 136.83, 132.90, 129.91, 129.42, 128.54, 128.25, 127.92, 127.38, 126.62, 125.97, 12.25, 9.01; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₈H₁₆N 246.1282, found 246.1278
SI, pp. S56, S195–S197
4-Cyclopropyl-3-phenylquinoline (3’as, minor)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.57 (d, J = 8.3 Hz, 1H), 8.13 (d, J = 8.3 Hz, 1H), 7.74 – 7.69 (m, 1H), 7.62 (td, J = 7.5, 1.0 Hz, 1H), 7.52 – 7.47 (m, 4H), 7.42 (ddd, J = 9.3, 4.0, 1.9 Hz, 1H), 2.28 (ddd, J = 14.3, 8.5, 5.8 Hz, 1H), 0.99 – 0.94 (m, 2H), 0.31 – 0.26 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.38, 147.46, 144.55, 138.97, 135.28, 130.06, 129.39, 128.96, 128.36, 127.46, 126.66, 125.64, 11.72, 9.56; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₈H₁₆N 246.1282, found 246.1277
SI, pp. S56–S57, S198–S200
3-Butyl-4-(o-tolyl)quinoline (3at, major)
¹H NMR (500 MHz, CDCl₃) δ 8.89 (s, 1H), 8.12 (d, J = 8.5 Hz, 1H), 7.63 (ddd, J = 8.4, 6.7, 1.4 Hz, 1H), 7.42 – 7.28 (m, 4H), 7.27 – 7.21 (m, 1H), 7.11 (dd, J = 7.5, 1.4 Hz, 1H), 2.58 (dt, J = 13.5, 7.8 Hz, 1H), 2.43 (dt, J = 13.5, 7.9 Hz, 1H), 1.92 (s, 3H), 1.54 – 1.43 (m, 2H), 1.31 – 1.19 (m, 2H), 0.79 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.57, 146.89, 145.67, 136.29, 136.19, 133.00, 130.26, 129.62, 129.54, 128.40, 128.30, 127.61, 126.65, 125.94, 125.91, 33.02, 30.84, 22.64, 19.81, 13.85; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂N 276.1752, found 276.1748
SI, pp. S57, S201–S203
4-Butyl-3-(o-tolyl)quinoline (3’at, minor)
¹H NMR (500 MHz, CDCl₃) δ 8.66 (s, 1H), 8.16 (d, J = 8.4 Hz, 1H), 8.09 (d, J = 8.4 Hz, 1H), 7.72 (t, J = 7.1 Hz, 1H), 7.60 (t, J = 7.3 Hz, 1H), 7.38 – 7.28 (m, 3H), 7.20 (d, J = 7.4 Hz, 1H), 3.08 – 2.97 (m, 1H), 2.69 (ddd, J = 12.9, 10.9, 5.8 Hz, 1H), 2.08 (s, 3H), 1.58 – 1.47 (m, 2H), 1.27 (ddd, J = 10.3, 7.5, 4.0 Hz, 2H), 0.78 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.58, 147.73, 146.19, 138.14, 136.49, 133.89, 130.33, 128.91, 128.19, 127.40, 126.71, 125.89, 124.39, 32.72, 28.85, 23.14, 20.38, 13.76; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₂₂N 276.1752, found 276.1748
SI, pp. S57, S204–S206
4-(4-Phenylquinolin-3-yl)butyl 2-(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (3au)
¹H NMR (500 MHz, CDCl₃) δ 8.84 (s, 1H), 8.13 – 8.08 (m, 2H), 7.86 – 7.82 (m, 1H), 7.64 (dt, J = 8.3, 4.0 Hz, 1H), 7.56 – 7.47 (m, 4H), 7.45 – 7.42 (m, 1H), 7.40 – 7.36 (m, 3H), 7.34 (d, J = 7.4 Hz, 1H), 7.25 (dd, J = 7.8, 1.4 Hz, 2H), 7.01 (d, J = 8.4 Hz, 1H), 5.15 (s, 2H), 3.97 (t, J = 6.0 Hz, 2H), 3.58 (s, 2H), 2.61 (t, J = 7.2 Hz, 2H), 1.59 – 1.51 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 190.88, 171.45, 160.55, 152.24, 146.93, 146.23, 140.51, 136.51, 136.39, 135.63, 132.85, 132.52, 132.10, 129.56, 129.46, 129.42, 129.34, 128.60, 128.49, 128.11, 127.89, 126.57, 126.27, 125.20, 121.15, 73.71, 64.65, 40.31, 30.65, 28.31, 27.71; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₃₅H₃₀NO₄ 528.2174, found 528.2172
SI, pp. S57–S58, S207
4-Methyl-3-(((triisopropylsilyl)oxy)methyl)quinoline (3av, major)
¹H NMR (500 MHz, CDCl₃) δ 8.99 (s, 1H), 8.08 (d, J = 7.9 Hz, 1H), 8.07 – 8.03 (m, 1H), 7.68 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.56 (ddd, J = 8.2, 6.8, 1.2 Hz, 1H), 5.03 (s, 2H), 2.65 (s, 3H), 1.25 – 1.17 (m, 3H), 1.11 (d, J = 7.0 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.34, 147.59, 141.07, 131.32, 130.20, 128.73, 127.91, 126.41, 123.72, 62.28, 18.20, 13.52, 12.17; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₃₂NOSi 330.2253, found 330.2248
SI, pp. S58, S208–S210
3-Methyl-4-(((triisopropylsilyl)oxy)methyl)quinoline (3’av, minor)
¹H NMR (500 MHz, CDCl₃) δ 8.74 (s, 1H), 8.27 – 8.23 (m, 1H), 8.08 – 8.04 (m, 1H), 7.63 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.54 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 5.22 (s, 2H), 2.56 (s, 3H), 1.24 – 1.16 (m, 3H), 1.09 (d, J = 7.1 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 153.32, 147.56, 142.00, 129.95, 128.44, 128.17, 127.28, 126.52, 124.51, 58.87, 18.18, 16.93, 12.21; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₀H₃₂NOSi 330.2253, found 330.2248
SI, pp. S58–S59, S211–S212
4-Methyl-3-(2-((triisopropylsilyl)oxy)ethyl)quinoline (3aw, major)
¹H NMR (500 MHz, CDCl₃) δ 8.73 (s, 1H), 8.06 (d, J = 8.6 Hz, 1H), 8.01 (d, J = 8.6 Hz, 1H), 7.65 (ddd, J = 8.3, 6.8, 1.5 Hz, 1H), 7.54 (ddd, J = 8.2, 6.8, 1.2 Hz, 1H), 3.92 (t, J = 7.0 Hz, 2H), 3.10 (t, J = 7.0 Hz, 2H), 2.67 (s, 3H), 1.12 – 1.05 (m, 3H), 1.00 (d, J = 6.4 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.98, 146.92, 141.46, 130.04, 129.84, 128.29, 128.18, 126.37, 123.76, 63.82, 35.05, 18.06, 14.21, 12.02; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₃₄NOSi 344.2410, found 344.2407
SI, pp. S59, S213–S215
3-Methyl-4-(2-((triisopropylsilyl)oxy)ethyl)quinoline (3’aw, minor)
¹H NMR (500 MHz, CDCl₃) δ 8.71 (s, 1H), 8.11 – 8.06 (m, 2H), 7.63 (ddd, J = 8.3, 6.7, 1.4 Hz, 1H), 7.58 – 7.50 (m, 1H), 4.00 – 3.89 (m, 2H), 3.38 (t, J = 7.2 Hz, 2H), 2.53 (s, 3H), 1.10 – 0.94 (m, 21H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.76, 147.21, 141.96, 130.16, 128.08, 126.50, 123.66, 62.72, 32.04, 18.02, 17.35, 12.00; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₃₄NOSi 344.2410, found 344.2408
SI, pp. S59, S216–S218
4-Methyl-3-pentylquinoline (3ax, major)
¹H NMR (500 MHz, CDCl₃) δ 8.68 (s, 1H), 8.06 (dd, J = 8.4, 1.3 Hz, 1H), 8.01 (dd, J = 8.4, 1.4 Hz, 1H), 7.64 (ddd, J = 8.3, 6.8, 1.4 Hz, 1H), 7.54 (ddd, J = 8.2, 6.7, 1.2 Hz, 1H), 2.85 – 2.78 (m, 2H), 2.64 (s, 3H), 1.62 (dt, J = 15.1, 7.6 Hz, 2H), 1.41 – 1.35 (m, 4H), 0.93 – 0.87 (m, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.62, 146.77, 140.49, 133.32, 130.02, 128.31, 128.10, 126.34, 123.71, 31.79, 31.52, 30.85, 22.68, 14.14, 13.95; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₅H₂₀N 214.1596, found 214.1591
SI, pp. S59–S60, S219–S221
3-Methyl-4-pentylquinoline (3’ax, minor)
¹H NMR (500 MHz, CDCl₃) δ 8.69 (s, 1H), 8.06 (dd, J = 8.4, 1.3 Hz, 1H), 8.00 (dd, J = 8.5, 1.4 Hz, 1H), 7.62 (ddd, J = 8.3, 6.8, 1.4 Hz, 1H), 7.53 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 3.08 – 3.01 (m, 2H), 2.47 (s, 3H), 1.68 – 1.58 (m, 2H), 1.51 – 1.34 (m, 4H), 0.93 (t, J = 7.2 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.83, 147.23, 145.90, 130.13, 128.05, 128.00, 127.37, 126.40, 123.51, 32.43, 29.55, 28.42, 22.67, 16.97, 14.14; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₅H₂₀N 214.1596, found 214.1590
SI, pp. S60, S222–S224
3-Isopropyl-4-methylquinoline (3ay)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.06 (d, J = 8.2 Hz, 1H), 8.02 (d, J = 8.5 Hz, 1H), 7.63 (t, J = 7.6 Hz, 1H), 7.53 (t, J = 7.7 Hz, 1H), 3.43 (hept, J = 6.9 Hz, 1H), 2.66 (s, 3H), 1.38 (d, J = 7.0 Hz, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 149.14, 146.44, 139.48, 129.93, 129.49, 128.64, 128.17, 126.41, 123.98, 28.62, 23.31, 13.38; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₃H₁₆N 186.1283, found 186.1276
SI, pp. S60–S61, S225–S227
3,4-Diethylquinoline (3a)
¹H NMR (500 MHz, CDCl₃) δ 8.73 (s, 1H), 8.07 (d, J = 8.4 Hz, 1H), 8.02 (d, J = 8.5 Hz, 1H), 7.63 (t, J = 7.4 Hz, 1H), 7.56 – 7.49 (m, 1H), 3.10 (qd, J = 7.6, 2.4 Hz, 2H), 2.89 – 2.80 (m, 2H), 1.31 (tt, J = 7.6, 2.5 Hz, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.36, 147.21, 146.12, 133.79, 130.23, 128.04, 126.42, 123.64, 24.07, 20.96, 16.12, 15.10; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₃H₁₆N 186.1283, found 186.1275
SI, pp. S61, S228
3,4-Diphenylquinoline (3az)
¹H NMR (500 MHz, CDCl₃) δ 9.03 (s, 1H), 8.25 – 8.19 (m, 1H), 7.78 – 7.69 (m, 2H), 7.50 (ddd, J = 8.3, 6.7, 1.3 Hz, 1H), 7.41 – 7.32 (m, 3H), 7.30 – 7.16 (m, 7H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 151.96, 147.71, 145.62, 138.29, 136.45, 133.27, 130.66, 130.30, 129.66, 129.23, 128.28, 128.19, 127.85, 127.38, 127.18, 127.00, 126.72; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₁H₁₆N 282.1283, found 282.1276
SI, pp. S61, S229
3,4-Diethyl-2-(trifluoromethyl)quinoline (3ba)
¹H NMR (500 MHz, CDCl₃) δ 8.19 – 8.15 (m, 1H), 8.08 – 8.04 (m, 1H), 7.72 (ddd, J = 8.3, 6.8, 1.4 Hz, 1H), 7.64 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 3.21 (q, J = 7.6 Hz, 2H), 3.03 – 2.97 (m, 2H), 1.35 (t, J = 7.6 Hz, 3H), 1.30 (t, J = 7.5 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.65, 146.47 (q, J = 31.5 Hz), 145.24, 131.51, 131.13, 129.26, 128.46, 128.19, 123.65, 122.64 (q, J = 277.2 Hz), 21.36 (q, J = 2.52 Hz), 21.11, 15.73, 15.20; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −63.60; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₄H₁₅F₃N 254.1157, found 254.1151
SI, pp. S61, S230–S231
3,4-Diethyl-2-methylquinoline (3bb)
¹H NMR (500 MHz, CDCl₃) δ 7.97 (t, J = 8.9 Hz, 2H), 7.60 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.47 (ddd, J = 8.2, 6.9, 1.2 Hz, 1H), 3.10 (q, J = 7.6 Hz, 2H), 2.86 (q, J = 7.6 Hz, 2H), 2.76 (s, 3H), 1.31 (t, J = 7.6 Hz, 3H), 1.23 (d, J = 7.6 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 158.44, 146.37, 146.31, 133.04, 129.27, 128.15, 126.37, 125.65, 123.63, 23.93, 22.48, 21.21, 15.20, 14.58; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₄H₁₈N 200.1439, found 200.1432
SI, pp. S62, S232
3-Butyl-4-phenylquinoline 1-oxide (9a)
¹H NMR (500 MHz, CDCl₃) δ 8.77 (d, J = 8.7 Hz, 1H), 8.55 (s, 1H), 7.68 (t, J = 7.5 Hz, 1H), 7.50 (dddd, J = 16.4, 11.1, 6.2, 2.1 Hz, 4H), 7.41 (d, J = 8.3 Hz, 1H), 7.27 (d, J = 1.6 Hz, 1H), 7.26 – 7.24 (m, 1H), 2.53 – 2.45 (m, 2H), 1.52 – 1.45 (m, 2H), 1.25 – 1.18 (m, 2H), 0.78 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 137.73, 136.84, 135.68, 134.10, 130.40, 130.03, 129.40, 128.76, 128.58, 128.40, 127.00, 119.65, 32.98, 30.79, 22.36, 13.77; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₀NO 278.1545, found 278.1541
SI, pp. S63, S233
3-Butyl-4-phenylquinolin-2(1H)-one (9b)
¹H NMR (500 MHz, CDCl₃) δ 11.64 (s, 1H), 7.55 – 7.36 (m, 5H), 7.24 (s, 2H), 7.03 (dt, J = 16.1, 7.6 Hz, 2H), 2.54 – 2.41 (m, 2H), 1.56 – 1.44 (m, 2H), 1.26 (td, J = 12.4, 5.1 Hz, 2H), 0.79 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 163.83, 148.83, 137.11, 136.91, 132.48, 129.42, 128.98, 128.64, 128.06, 127.20, 122.30, 121.59, 115.56, 31.50, 28.12, 23.02, 13.93; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₀NO 278.1545, found 278.1541
SI, pp. S64, S234
trans-3-Butyl-4-phenyl-1,2,3,4-tetrahydroquinoline (9c)
GC–FID and GC–MS, crude reaction mixture dr >99:1; only a single diastereomer was observed
¹H NMR (500 MHz, CDCl₃) δ 7.34 – 7.29 (m, 2H), 7.26 – 7.21 (m, 1H), 7.15 – 7.11 (m, 2H), 7.06 – 7.01 (m, 1H), 6.76 – 6.72 (m, 1H), 6.59 (t, J = 7.4 Hz, 2H), 3.95 (s, 1H), 3.83 (d, J = 6.4 Hz, 1H), 3.34 (dd, J = 11.4, 3.4 Hz, 1H), 3.02 (dd, J = 11.4, 6.7 Hz, 1H), 2.00 (dt, J = 6.4, 3.2 Hz, 1H), 1.41 (dt, J = 10.1, 5.2 Hz, 2H), 1.31 (tt, J = 9.5, 4.0 Hz, 4H), 0.89 (t, J = 7.1 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 146.77, 144.81, 131.27, 129.18, 128.30, 127.16, 126.12, 123.25, 117.26, 114.00, 49.23, 43.40, 39.84, 31.91, 29.54, 22.90, 14.18; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₂₄N 266.1909, found 266.1905
SI, pp. S65, S235
3-Butyl-2-cyclopropyl-4-phenylquinoline (3bc)
¹H NMR (500 MHz, CDCl₃) δ 7.95 – 7.92 (m, 1H), 7.57 – 7.45 (m, 4H), 7.26 (ddt, J = 6.8, 5.7, 1.4 Hz, 3H), 7.21 (dd, J = 8.4, 1.1 Hz, 1H), 2.74 – 2.68 (m, 2H), 2.37 (tt, J = 8.1, 4.9 Hz, 1H), 1.59 – 1.52 (m, 2H), 1.37 (dq, J = 4.8, 3.5 Hz, 2H), 1.29 – 1.24 (m, 2H), 1.07 (dq, J = 8.0, 3.5 Hz, 2H), 0.80 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 161.81, 146.35, 145.79, 137.99, 132.28, 129.58, 128.79, 128.40, 128.03, 127.67, 126.81, 126.25, 125.05, 32.99, 29.68, 23.12, 14.74, 13.80, 10.03; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₂H₂₄N 302.1909, found 302.1906
SI, pp. S66, S236
3-Butyl-2-phenoxy-4-phenylquinoline (3bd)
¹H NMR (500 MHz, CDCl₃) δ 7.76 (d, J = 8.3 Hz, 1H), 7.58 – 7.44 (m, 6H), 7.35 – 7.29 (m, 4H), 7.28 – 7.24 (m, 3H), 2.70 – 2.63 (m, 2H), 1.60 (dtd, J = 10.6, 7.6, 4.8 Hz, 2H), 1.28 (h, J = 7.4 Hz, 2H), 0.81 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 160.64, 154.37, 149.52, 144.79, 137.16, 129.50, 129.46, 128.52, 128.51, 127.97, 127.75, 126.45, 126.26, 125.40, 124.52, 124.43, 121.74, 32.28, 27.88, 22.94, 13.89; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₂₄NO 354.1858, found 354.1850
SI, pp. S67, S237
3-Butyl-4-phenyl-2-(phenylthio)quinoline (3be)
¹H NMR (500 MHz, CDCl₃) δ 7.71 (d, J = 8.1 Hz, 1H), 7.69 – 7.64 (m, 2H), 7.55 – 7.38 (m, 7H), 7.30 – 7.26 (m, 2H), 7.26 – 7.19 (m, 2H), 2.72 – 2.63 (m, 2H), 1.63 – 1.53 (m, 2H), 1.28 (h, J = 7.4 Hz, 2H), 0.81 (t, J = 7.4 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.36, 146.54, 146.34, 137.15, 135.01, 131.93, 131.37, 129.49, 128.92, 128.50, 128.41, 128.37, 127.95, 126.79, 126.27, 125.42, 32.10, 30.05, 23.10, 13.71; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₂₄NS 370.1629, found 370.1625
SI, pp. S68, S238
3-Butyl-4-phenyl-2-(4-(quinolin-2-yl)piperazin-1-yl)quinoline (3bf)
¹H NMR (500 MHz, CDCl₃) δ 7.93 (t, J = 8.2 Hz, 2H), 7.76 (d, J = 8.3 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.58 – 7.45 (m, 5H), 7.31 – 7.27 (m, 2H), 7.24 (ddd, J = 11.3, 5.7, 4.2 Hz, 3H), 7.10 (d, J = 9.1 Hz, 1H), 3.99 – 3.91 (m, 4H), 3.51 – 3.44 (m, 4H), 2.66 (dd, J = 9.2, 6.6 Hz, 2H), 1.46 – 1.37 (m, 2H), 1.17 (h, J = 7.3 Hz, 2H), 0.74 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 161.91, 157.96, 148.87, 148.01, 145.78, 137.88, 137.57, 129.71, 129.67, 128.94, 128.45, 128.38, 127.98, 127.77, 127.37, 126.83, 126.48, 126.16, 124.60, 123.36, 122.61, 109.97, 51.24, 45.75, 32.50, 29.13, 23.13, 13.91; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₃₂H₃₃N₄ 473.2705, found 473.2694
SI, pp. S69, S239
4-(4-Fluorophenyl)-3-(((triisopropylsilyl)oxy)methyl)quinoline (3bg)
¹H NMR (500 MHz, CDCl₃) δ 9.11 (s, 1H), 8.05 (d, J = 8.4 Hz, 1H), 7.58 (ddd, J = 8.3, 6.0, 2.2 Hz, 1H), 7.37 – 7.31 (m, 2H), 7.18 (ddd, J = 10.1, 6.2, 3.5 Hz, 2H), 7.14 – 7.10 (m, 2H), 4.59 (s, 2H), 1.03 – 0.95 (m, 3H), 0.92 (d, J = 6.5 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.80 (d, J = 248.22 Hz), 150.98, 147.72, 144.24, 131.49 (d, J = 3.78 Hz), 131.31 (d, J = 7.56 Hz), 131.16, 129.74, 129.03, 127.25, 126.76, 126.04, 115.70 (d, J = 21.42 Hz), 61.87, 18.11, 12.07; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −113.49; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₃₃FNOSi 410.2315, found 410.2309
SI, pp. S70–S71, S240–S241
4-(4-Fluorophenyl)-3-(((triisopropylsilyl)oxy)methyl)quinoline 1-oxide (9d)
¹H NMR (500 MHz, CDCl₃) δ 8.85 (s, 1H), 8.82 (d, J = 8.6 Hz, 1H), 7.73 (ddd, J = 8.5, 6.8, 1.3 Hz, 1H), 7.52 (ddd, J = 8.2, 6.8, 1.2 Hz, 1H), 7.46 – 7.43 (m, 1H), 7.28 – 7.21 (m, 4H), 4.59 (s, 2H), 1.12 – 1.04 (m, 3H), 1.01 (d, J = 6.4 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.6 (d, J = 249.5 Hz), 140.67, 135.18, 134.03, 133.15, 131.59 (d, J = 7.56 Hz), 130.61 (d, J = 3.78 Hz), 129.90, 129.83, 128.80, 126.58, 120.06, 116.09 (d, J = 21.4 Hz), 61.29, 18.09, 11.99; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −112.64; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₅H₃₃FNO₂Si 426.2265, found 426.2259
SI, pp. S71–S72, S242–S243
2-Cyclopropyl-4-(4-fluorophenyl)-3-(((triisopropylsilyl)oxy)methyl)quinoline (3bh)
¹H NMR (500 MHz, CDCl₃) δ 7.96 (d, J = 8.3 Hz, 1H), 7.59 (ddd, J = 8.4, 6.2, 2.1 Hz, 1H), 7.29 (ddd, J = 8.7, 3.1, 2.2 Hz, 4H), 7.22 – 7.17 (m, 2H), 4.85 (s, 2H), 2.75 (tt, J = 8.1, 4.9 Hz, 1H), 1.37 (dq, J = 4.9, 3.5 Hz, 2H), 1.08 – 0.99 (m, 5H), 0.97 (d, J = 5.6 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 163.28, 162.67 (d, J = 248.2 Hz), 147.27, 145.63, 132.75 (d, J = 3.78 Hz), 131.81 (d, J = 7.56 Hz), 129.82, 128.96 (d, J = 7.56 Hz), 126.51, 126.36, 125.31, 115.33 (d, J = 21.4 Hz), 60.52, 18.10, 14.86, 12.22, 10.18; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −114.22; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₂₈H₃₇FNOSi 450.2628, found 450.2626
SI, pp. S72–S73, S244–S245
(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol (3bi)
¹H NMR (500 MHz, CDCl₃) δ 7.99 – 7.94 (m, 1H), 7.61 (ddd, J = 8.4, 6.1, 2.2 Hz, 1H), 7.35 – 7.27 (m, 4H), 7.25 – 7.18 (m, 2H), 4.74 (s, 2H), 2.58 (tt, J = 8.1, 4.9 Hz, 1H), 1.86 (s, 1H), 1.37 (dq, J = 4.8, 3.6 Hz, 2H), 1.12 – 1.04 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.71 (d, J = 247 Hz), 162.36, 147.47, 146.53, 132.50 (d, J = 3.78 Hz), 131.45 (d, J = 7.56 Hz), 129.42, 129.32, 129.02, 126.53, 126.26, 125.63, 115.62 (d, J = 21.42 Hz), 59.80, 14.68, 9.96; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −113.65; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₇FNO 294.1294, found 294.1292
SI, pp. S73–S74, S246–S247
2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (3bj)
¹H NMR (500 MHz, CDCl₃) δ 10.07 (s, 1H), 8.01 – 7.95 (m, 1H), 7.74 (ddd, J = 8.4, 6.7, 1.5 Hz, 1H), 7.45 (dd, J = 8.4, 0.9 Hz, 1H), 7.39 (ddd, J = 8.3, 6.7, 1.2 Hz, 1H), 7.34 (ddt, J = 7.9, 5.0, 2.4 Hz, 2H), 7.29 – 7.23 (m, 2H), 3.22 (tt, J = 8.1, 4.8 Hz, 1H), 1.39 (dt, J = 4.9, 3.2 Hz, 2H), 1.11 (dq, J = 8.1, 3.4 Hz, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 193.79, 163.21 (d, J = 249.48 Hz), 161.80, 152.96, 149.10, 132.12 (d, J = 7.5 Hz), 131.99, 130.13 (d, J = 3.78 Hz), 129.34, 126.66, 126.34, 126.26, 125.43, 115.92 (d, J = 21.42), 14.66, 11.47; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −112.05; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₉H₁₅FNO 292.1138, found 292.1134
SI, pp. S74–S75, S248–S249
Benzo[d]thiazole-2-d (1a-d)
¹H NMR, deuteration percentage 81 %[D] at C2; repeated preparation: 92 %[D] at C2; image data were not transcribed
¹H NMR (500 MHz, CDCl₃), 81 %[D] δ 9.00 (s, 0.19H), 8.15 (ddd, J = 8.2, 1.3, 0.7 Hz, 1H), 7.97 (ddd, J = 7.9, 1.3, 0.7 Hz, 1H), 7.58 – 7.49 (m, 1H), 7.49 – 7.40 (m, 1H); image data were not transcribed
¹³C NMR (101 MHz, CDCl₃) δ 153.74, 153.49 (t, J = 32.3 Hz), 153.06 (t, J = 2.0 Hz), 133.53, 133.49, 125.94, 125.30, 123.42, 121.69
SI, pp. S76–S77, S250–S251
6-Methylbenzo[d]thiazole (1b)
¹H NMR (500 MHz, CDCl₃) δ 8.90 (s, 1H), 8.01 (d, J = 8.4 Hz, 1H), 7.73 (s, 1H), 7.35 – 7.30 (m, 1H), 2.50 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.96, 151.55, 135.81, 134.01, 127.94, 123.18, 121.65, 21.63; image data were not transcribed
SI, pp. S78, S252
6-Methoxybenzo[d]thiazole (1c)
¹H NMR (500 MHz, CDCl₃) δ 8.80 (s, 1H), 8.00 (d, J = 9.0 Hz, 1H), 7.37 (d, J = 2.6 Hz, 1H), 7.11 (dd, J = 9.0, 2.6 Hz, 1H), 3.86 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 158.15, 151.43, 148.02, 135.23, 124.11, 115.91, 104.15, 55.89; image data were not transcribed
SI, pp. S78, S253
6-(Trifluoromethyl)benzo[d]thiazole (1g)
¹H NMR (500 MHz, CDCl₃) δ 9.16 (s, 1H), 8.30 – 8.27 (m, 1H), 8.25 (d, J = 8.5 Hz, 1H), 7.77 (dd, J = 8.6, 2.1 Hz, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ δ 156.96, 155.35, 134.09, 128.11 (q, J = 32.6 Hz), 124.32, 123.37 (q, J = 3.5 Hz), 124.26 (q, J = 273.42), 119.85 (q, J = 4.5 Hz); image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −61.47; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₈H₅F₃NS 204.0095, found 204.0089
SI, pp. S79, S254–S255
6-(Trifluoromethoxy)benzo[d]thiazole (1h)
¹H NMR (500 MHz, CDCl₃) δ 9.02 (s, 1H), 8.13 (d, J = 8.9 Hz, 1H), 7.85 – 7.80 (m, 1H), 7.39 (ddd, J = 8.9, 2.4, 0.9 Hz, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 155.13, 151.88, 146.98, 134.78, 124.63, 120.64 (q, J = 6.3 Hz), 119.62, 114.48; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −58.03; image data were not transcribed
SI, pp. S79, S256–S257
Benzo[d]thiazole-6-carbonitrile (1i)
¹H NMR (500 MHz, CDCl₃) δ 9.21 (s, 1H), 8.33 (dd, J = 1.7, 0.6 Hz, 1H), 8.22 (dd, J = 8.5, 0.8 Hz, 1H), 7.78 (dd, J = 8.5, 1.6 Hz, 1H); image data were not transcribed
¹³C NMR (101 MHz, CDCl₃) δ 158.11, 155.52, 134.40, 129.34, 127.03, 124.61, 118.58, 109.35; image data were not transcribed
SI, pp. S79, S258
Ethyl benzo[d]thiazole-6-carboxylate (1j)
¹H NMR (400 MHz, CDCl₃) δ 9.15 (s, 1H), 8.71 (dd, J = 1.6, 0.7 Hz, 1H), 8.24 – 8.14 (m, 2H), 4.44 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.2 Hz, 3H); image data were not transcribed
¹³C NMR (101 MHz, CDCl₃) δ 166.22, 157.26, 156.18, 133.91, 128.08, 127.49, 124.32, 123.56, 61.52, 14.51; image data were not transcribed
SI, pp. S79–S80, S259
6-Fluorobenzo[d]thiazole (1m)
¹H NMR (500 MHz, CDCl₃) δ 8.94 (s, 1H), 8.08 (dd, J = 9.0, 4.8 Hz, 1H), 7.63 (dd, J = 8.1, 2.5 Hz, 1H), 7.29 – 7.23 (m, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 160.91 (d, J = 246.96 Hz), 153.70 (d, J = 2.52 Hz), 150.09, 134.93 (d, J = 11.34 Hz), 124.71 (d, J = 8.82 Hz), 115.18 (d, J = 25.2 Hz), 108.07 (d, J = 26.46 Hz); image data were not transcribed
SI, pp. S80, S260
6-Chlorobenzo[d]thiazole (1n)
¹H NMR (500 MHz, CDCl₃) δ 8.98 (s, 1H), 8.07 – 8.02 (m, 1H), 7.94 (d, J = 2.0 Hz, 1H), 7.48 (dd, J = 8.7, 2.1 Hz, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.42, 151.98, 135.11, 131.81, 127.21, 124.50, 121.61; image data were not transcribed
SI, pp. S80, S261
5-Methoxybenzo[d]thiazole (1o)
¹H NMR (500 MHz, CDCl₃) δ 8.96 (s, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.61 (d, J = 2.5 Hz, 1H), 7.09 (dd, J = 8.8, 2.5 Hz, 1H), 3.90 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.14, 155.08, 154.78, 125.66, 122.13, 116.20, 105.77, 55.74; image data were not transcribed
SI, pp. S80–S81, S262
5-Fluorobenzo[d]thiazole (1p)
¹H NMR (500 MHz, CDCl₃) δ 9.03 (s, 1H), 7.87 (dd, J = 8.8, 5.1 Hz, 1H), 7.81 (dd, J = 9.4, 2.5 Hz, 1H), 7.21 (td, J = 8.8, 2.5 Hz, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 161.91 (d, J = 243.8 Hz), 156.35, 154.37 (d, J = 11.9 Hz), 129.27 (d, J = 1.9 Hz), 122.66 (d, J = 9.8 Hz), 114.59 (d, J = 25.2 Hz), 109.81 (d, J = 23.6 Hz); image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −115.96; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₇H₅FNS 154.0127, found 154.0120
SI, pp. S81, S263–S264
4-Chlorobenzo[d]thiazole (1s)
¹H NMR (500 MHz, CDCl₃) δ 9.04 (s, 1H), 7.82 (dd, J = 8.1, 1.0 Hz, 1H), 7.51 (dd, J = 7.8, 1.0 Hz, 1H), 7.36 – 7.32 (m, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.93, 150.37, 135.41, 128.75, 126.58, 126.31, 120.61; image data were not transcribed
SI, pp. S81, S265
4-Methylbenzo[d]thiazole (1t)
¹H NMR (400 MHz, CDCl₃) δ 8.98 (s, 1H), 7.79 (dd, J = 7.2, 2.0 Hz, 1H), 7.38 – 7.28 (m, 2H), 2.80 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.76, 152.65, 133.65, 133.53, 126.73, 125.54, 119.37, 18.45; image data were not transcribed
SI, pp. S81, S266
4-Methoxybenzo[d]thiazole (1u)
¹H NMR (500 MHz, CDCl₃) δ 8.87 (s, 1H), 7.49 (dd, J = 8.1, 0.9 Hz, 1H), 7.37 – 7.33 (m, 1H), 6.90 (dd, J = 8.0, 0.7 Hz, 1H), 4.03 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.00, 152.40, 143.69, 135.60, 126.66, 113.82, 106.52, 56.06; image data were not transcribed
SI, pp. S81–S82, S267
4-Nitrobenzo[d]thiazole (1v)
¹H NMR (500 MHz, CDCl₃) δ 9.30 (s, 1H), 8.28 (d, J = 7.9 Hz, 2H), 7.62 (t, J = 8.0 Hz, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 158.15, 145.40, 143.10, 137.33, 127.86, 125.22, 122.97; image data were not transcribed
HRMS (ESI⁺) m/z: [M+Na]⁺ calcd for C₇H₄N₂NaO₂S 202.9891, found 202.9888
SI, pp. S82, S268
5,6-Dimethylbenzo[d]thiazole (1x)
¹H NMR (400 MHz, CDCl₃) δ 8.87 (s, 1H), 7.90 (s, 1H), 7.71 (s, 1H), 2.42 (s, 3H), 2.41 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.82, 152.20, 135.55, 135.15, 131.21, 123.72, 121.73, 20.28, 20.26; image data were not transcribed
SI, pp. S82, S269
4,7-Dimethylbenzo[d]thiazole (1y)
¹H NMR (500 MHz, CDCl₃) δ 8.98 (s, 1H), 7.24 (d, J = 7.3 Hz, 1H), 7.14 (d, J = 7.3 Hz, 1H), 2.76 (s, 3H), 2.56 (s, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.41, 152.32, 134.22, 130.66, 129.22, 126.95, 125.63, 21.30, 18.18; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₉H₁₀NS 164.0534, found 164.0528
SI, pp. S82–S83, S270
Benzyl benzo[d]thiazole-6-carboxylate (1k)
¹H NMR (500 MHz, CDCl₃) δ 9.13 (s, 1H), 8.74 – 8.70 (m, 1H), 8.23 (dd, J = 8.6, 1.6 Hz, 1H), 8.18 – 8.14 (m, 1H), 7.50 – 7.45 (m, 2H), 7.43 – 7.38 (m, 2H), 7.38 – 7.34 (m, 1H), 5.42 (s, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 165.98, 157.45, 156.21, 135.92, 133.88, 128.78, 128.52, 128.42, 127.55, 124.46, 123.56, 67.22; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₅H₁₂NO₂S 270.0589, found 270.0585
SI, pp. S83–S84, S271
Benzo[d]thiazol-6-yl(piperidin-1-yl)methanone (1l)
¹H NMR (500 MHz, CDCl₃) δ 9.03 (s, 1H), 8.11 (dd, J = 8.4, 0.5 Hz, 1H), 8.00 (dd, J = 1.6, 0.5 Hz, 1H), 7.50 (dd, J = 8.4, 1.6 Hz, 1H), 3.71 (br s, 2H), 3.34 (br s, 2H), 1.66 (br s, 4H), 1.51 (br s, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 169.56, 155.47, 153.72, 134.01, 133.97, 125.10, 123.57, 120.95, 48.97, 43.39, 26.61, 25.66, 24.60; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₃H₁₅N₂OS 247.0905, found 247.0902
SI, pp. S84, S272
6-((Triethylsilyl)oxy)benzo[d]thiazole (1d)
¹H NMR (500 MHz, CDCl₃) δ 8.82 (s, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.37 (d, J = 2.3 Hz, 1H), 7.05 (dd, J = 8.8, 2.4 Hz, 1H), 1.02 (t, J = 7.9 Hz, 9H), 0.80 – 0.75 (m, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.04, 151.85, 148.40, 134.99, 124.00, 120.19, 111.61, 6.73, 5.09; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₃H₂₀NOSSi 266.1035, found 266.1029
SI, pp. S85, S273
4-(Benzyloxy)benzo[d]thiazole (1w)
¹H NMR (500 MHz, CDCl₃) δ 8.91 (s, 1H), 7.54 – 7.48 (m, 3H), 7.40 – 7.34 (m, 2H), 7.33 – 7.28 (m, 2H), 6.96 – 6.92 (m, 1H), 5.38 (s, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.95, 152.36, 143.89, 136.71, 135.70, 128.60, 127.93, 127.38, 126.45, 114.05, 108.59, 70.84; image data were not transcribed
SI, pp. S86, S274
Naphtho[1,2-d]thiazole (1ac)
¹H NMR (400 MHz, CDCl₃) δ 9.11 (s, 1H), 8.85 (d, J = 8.2 Hz, 1H), 8.03 – 7.94 (m, 2H), 7.87 (d, J = 8.8 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.64 – 7.58 (m, 1H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 152.67, 149.94, 132.09, 130.81, 128.97, 128.21, 127.33, 126.56, 126.43, 123.84, 119.13; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₁H₈NS 186.0377, found 186.0372
SI, pp. S87, S275
Pent-3-yn-1-yl 4-methylbenzenesulfonate (2v)
¹H NMR (500 MHz, CDCl₃) δ 7.82 – 7.77 (m, 2H), 7.35 (d, J = 8.2 Hz, 2H), 4.04 (t, J = 7.2 Hz, 2H), 2.48 – 2.42 (m, 2H), 2.45 (s, 3H), 1.71 (t, J = 2.5 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 144.99, 133.08, 129.97, 128.09, 78.32, 73.23, 68.38, 21.77, 19.81, 3.52; image data were not transcribed
SI, pp. S88, S276
N-(Pent-3-yn-1-yl)benzo[d]thiazol-7-amine (1ad)
¹H NMR (500 MHz, CDCl₃) δ 8.94 (s, 1H), 7.60 (dd, J = 8.1, 0.8 Hz, 1H), 7.41 (t, J = 8.0 Hz, 1H), 6.68 (d, J = 7.8 Hz, 1H), 4.00 (s, 1H), 3.43 (q, J = 6.4 Hz, 2H), 2.58 – 2.52 (m, 2H), 1.82 (t, J = 2.5 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 154.61, 152.28, 142.73, 127.59, 121.02, 113.74, 106.33, 78.24, 76.03, 43.28, 19.56, 3.64; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₁₂H₁₃N₂S 217.0799, found 217.0796
SI, pp. S89, S277
2-(Trifluoromethyl)benzo[d]thiazole (1ae)
¹H NMR (500 MHz, DMSO-d₆) δ 8.35 – 8.29 (m, 1H), 8.28 – 8.21 (m, 1H), 7.75 – 7.64 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 154.95 (q, J = 39.48 Hz), 151.46, 134.57, 127.88, 127.79, 124.49, 123.31, 119.78 (q, J = 272.96 Hz); image data were not transcribed
¹⁹F NMR (471 MHz, DMSO-d₆) δ −60.8; image data were not transcribed
HRMS (ESI⁺) m/z: [M+H]⁺ calcd for C₈H₅F₃NS 204.0095, found 204.0089
SI, pp. S90, S278–S279
1-(tert-Butyl)-4-(hex-1-yn-1-yl)benzene (2c)
¹H NMR (500 MHz, CDCl₃) δ 7.42 – 7.33 (m, 4H), 2.46 (t, J = 7.0 Hz, 2H), 1.69 – 1.61 (m, 2H), 1.58 – 1.50 (m, 2H), 1.36 (s, 9H), 1.01 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 150.66, 131.37, 125.27, 121.28, 89.69, 80.69, 34.76, 31.33, 31.08, 22.15, 19.26, 13.79; image data were not transcribed
SI, pp. S91–S92, S280
1-(Hex-1-yn-1-yl)-4-methoxybenzene (2d)
¹H NMR (500 MHz, CDCl₃) δ 7.35 – 7.31 (m, 2H), 6.83 – 6.79 (m, 2H), 3.79 (s, 3H), 2.39 (t, J = 7.0 Hz, 2H), 1.61 – 1.55 (m, 2H), 1.51 – 1.45 (m, 2H), 0.95 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.03, 132.90, 116.33, 113.83, 88.77, 80.31, 55.23, 31.05, 22.11, 19.17, 13.74; image data were not transcribed
SI, pp. S92, S281
4-(Hex-1-yn-1-yl)-N,N-dimethylaniline (2e)
¹H NMR (500 MHz, CDCl₃) δ 7.28 (d, J = 8.8 Hz, 2H), 6.62 (d, J = 8.9 Hz, 2H), 2.95 (s, 6H), 2.41 (t, J = 7.1 Hz, 2H), 1.62 – 1.55 (m, 2H), 1.53 – 1.45 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 149.81, 132.61, 112.10, 111.47, 87.79, 81.14, 40.45, 31.30, 22.18, 19.35, 13.81; image data were not transcribed
SI, pp. S92, S282
1-Fluoro-4-(hex-1-yn-1-yl)benzene (2f)
¹H NMR (500 MHz, CDCl₃) δ 7.42 – 7.33 (m, 2H), 7.01 – 6.95 (m, 2H), 2.41 (t, J = 7.1 Hz, 2H), 1.63 – 1.57 (m, 2H), 1.54 – 1.46 (m, 2H), 0.97 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 162.10 (d, J = 248.2 Hz), 133.39 (d, J = 7.56 Hz), 120.29 (d, J = 3.78 Hz), 115.44 (d, J = 21.42 Hz), 90.08, 79.61, 30.93, 22.15, 19.13, 13.72; image data were not transcribed
¹⁹F NMR (471 MHz, CDCl₃) δ −112.40; image data were not transcribed
SI, pp. S92, S283–S284
1-Chloro-4-(hex-1-yn-1-yl)benzene (2g)
¹H NMR (500 MHz, CDCl₃) δ 7.35 – 7.32 (m, 2H), 7.28 – 7.25 (m, 2H), 2.42 (t, J = 7.1 Hz, 2H), 1.65 – 1.58 (m, 2H), 1.50 (dddd, J = 14.2, 9.7, 7.6, 6.0 Hz, 2H), 0.98 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 133.48, 132.88, 128.58, 122.74, 91.61, 79.63, 30.86, 22.14, 19.21, 13.75; image data were not transcribed
SI, pp. S92–S93, S285
1-(4-(Hex-1-yn-1-yl)phenyl)ethan-1-one (2h)
¹H NMR (500 MHz, CDCl₃) δ 7.84 – 7.79 (m, 2H), 7.43 – 7.39 (m, 2H), 2.52 (s, 3H), 2.39 (t, J = 7.1 Hz, 2H), 1.59 – 1.52 (m, 2H), 1.48 – 1.40 (m, 2H), 0.91 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 197.21, 135.65, 131.62, 129.17, 128.14, 94.35, 80.13, 30.65, 26.50, 22.03, 19.22, 13.61; image data were not transcribed
SI, pp. S93, S286
1-(Hex-1-yn-1-yl)-3-methoxybenzene (2i)
¹H NMR (500 MHz, CDCl₃) δ 7.27 – 7.22 (m, 1H), 7.06 (dt, J = 7.6, 1.2 Hz, 1H), 7.00 (dd, J = 2.7, 1.4 Hz, 1H), 6.89 (ddd, J = 8.4, 2.6, 1.0 Hz, 1H), 3.84 (s, 3H), 2.47 (t, J = 7.1 Hz, 2H), 1.69 – 1.62 (m, 2H), 1.59 – 1.51 (m, 2H), 1.02 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 159.35, 129.30, 125.19, 124.16, 116.45, 114.11, 90.35, 80.57, 55.22, 30.92, 22.13, 19.17, 13.74; image data were not transcribed
SI, pp. S93, S287
2-(Hex-1-yn-1-yl)naphthalene (2j)
¹H NMR (500 MHz, CDCl₃) δ 7.96 (d, J = 1.5 Hz, 1H), 7.83 – 7.77 (m, 3H), 7.53 – 7.46 (m, 3H), 2.51 (t, J = 7.1 Hz, 2H), 1.72 – 1.65 (m, 2H), 1.61 – 1.52 (m, 2H), 1.03 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 133.16, 132.53, 131.09, 128.84, 127.88, 127.77, 127.64, 126.42, 126.29, 121.55, 90.93, 81.05, 30.99, 22.18, 19.32, 13.80; image data were not transcribed
SI, pp. S93–S94, S288
2-(Hex-1-yn-1-yl)thiophene (2k)
¹H NMR (500 MHz, CDCl₃) δ 7.17 (dd, J = 5.2, 1.2 Hz, 1H), 7.14 (dd, J = 3.7, 1.2 Hz, 1H), 6.94 (dd, J = 5.2, 3.6 Hz, 1H), 2.45 (t, J = 7.1 Hz, 2H), 1.65 – 1.58 (m, 2H), 1.54 – 1.46 (m, 2H), 0.98 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 130.92, 126.81, 125.89, 124.33, 94.56, 73.75, 30.74, 22.13, 19.45, 13.73; image data were not transcribed
SI, pp. S94, S289
6-Phenylhex-5-yn-1-ol (2l)
¹H NMR (500 MHz, CDCl₃) δ 7.41 – 7.38 (m, 2H), 7.30 – 7.25 (m, 3H), 3.68 (t, J = 6.2 Hz, 2H), 2.45 (t, J = 6.7 Hz, 2H), 1.96 (s, 1H), 1.77 – 1.64 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 131.61, 128.29, 127.67, 123.95, 89.99, 81.03, 62.45, 31.94, 25.09, 19.26; image data were not transcribed
SI, pp. S94, S290
(6-Chlorohex-1-yn-1-yl)benzene (2m)
¹H NMR (500 MHz, CDCl₃) δ 7.42 – 7.37 (m, 2H), 7.30 – 7.24 (m, 3H), 3.57 (t, J = 6.6 Hz, 2H), 2.44 (t, J = 7.0 Hz, 2H), 1.94 (dq, J = 8.4, 6.6 Hz, 2H), 1.79 – 1.69 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 131.60, 128.30, 127.73, 123.86, 89.37, 81.28, 44.64, 31.70, 25.96, 18.78; image data were not transcribed
SI, pp. S94, S291
6-Phenylhex-5-ynenitrile (2n)
¹H NMR (500 MHz, CDCl₃) δ 7.42 – 7.38 (m, 2H), 7.30 (tt, J = 3.5, 2.2 Hz, 3H), 2.64 – 2.52 (m, 4H), 1.97 (p, J = 7.0 Hz, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 131.60, 128.32, 128.04, 123.28, 119.20, 87.03, 82.42, 24.68, 18.56, 16.21; image data were not transcribed
SI, pp. S94–S95, S292
(Cyclopropylethynyl)benzene (2o)
¹H NMR (500 MHz, CDCl₃) δ 7.49 – 7.32 (m, 2H), 7.31 – 7.16 (m, 3H), 1.53 – 1.38 (m, 1H), 0.90 – 0.76 (m, 4H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 131.66, 128.25, 127.52, 124.00, 93.48, 75.85, 8.68, 0.27; image data were not transcribed
SI, pp. S95, S293
1-(Hex-1-yn-1-yl)-2-methylbenzene (2p)
¹H NMR (500 MHz, CDCl₃) δ 7.46 (d, J = 7.5 Hz, 1H), 7.27 – 7.16 (m, 3H), 2.55 (t, J = 7.0 Hz, 2H), 2.52 (s, 3H), 1.75 – 1.67 (m, 2H), 1.65 – 1.57 (m, 2H), 1.06 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 139.90, 131.85, 129.32, 127.49, 125.48, 123.98, 94.37, 79.57, 31.10, 22.10, 20.78, 19.31, 13.71; image data were not transcribed
SI, pp. S95, S294
Triisopropyl(pent-3-yn-1-yloxy)silane (2q)
¹H NMR (500 MHz, CDCl₃) δ 3.76 (t, J = 7.5 Hz, 2H), 2.37 (tq, J = 7.6, 2.5 Hz, 2H), 1.76 (t, J = 2.6 Hz, 3H), 1.12 – 1.02 (m, 21H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 76.80, 76.22, 62.73, 23.34, 18.08, 12.12, 3.59; image data were not transcribed
SI, pp. S96, S295
(But-2-yn-1-yloxy)triisopropylsilane (2r)
¹H NMR (500 MHz, CDCl₃) δ 4.33 (q, J = 2.3 Hz, 2H), 1.83 (t, J = 2.4 Hz, 3H), 1.15 – 1.05 (m, 21H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 80.75, 78.05, 52.28, 18.07, 12.15, 3.76; image data were not transcribed
SI, pp. S96, S296
Triisopropyl((3-phenylprop-2-yn-1-yl)oxy)silane (2s)
¹H NMR (500 MHz, CDCl₃) δ 7.45 – 7.40 (m, 2H), 7.33 – 7.28 (m, 3H), 4.61 (s, 2H), 1.21 – 1.15 (m, 3H), 1.12 (d, J = 6.3 Hz, 18H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 131.74, 128.37, 128.31, 123.21, 88.19, 84.67, 52.60, 18.10, 12.21; image data were not transcribed
SI, pp. S96–S97, S297
(6-(Benzyloxy)hex-1-yn-1-yl)benzene (2t)
¹H NMR (500 MHz, CDCl₃) δ 7.49 – 7.46 (m, 2H), 7.44 – 7.39 (m, 4H), 7.37 – 7.30 (m, 4H), 4.58 (s, 2H), 3.60 (t, J = 6.3 Hz, 2H), 2.51 (t, J = 7.0 Hz, 2H), 1.91 – 1.83 (m, 2H), 1.82 – 1.75 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 138.69, 131.60, 128.40, 128.23, 127.64, 127.55, 124.11, 90.08, 80.97, 72.93, 69.90, 29.03, 25.58, 19.29; image data were not transcribed
SI, pp. S97, S298
6-Phenylhex-5-yn-1-yl 2-(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (2u)
¹H NMR (500 MHz, CDCl₃) δ 8.13 (d, J = 2.4 Hz, 1H), 7.89 (dd, J = 7.7, 1.2 Hz, 1H), 7.55 (td, J = 7.5, 1.4 Hz, 1H), 7.46 (td, J = 7.6, 1.2 Hz, 1H), 7.43 (dd, J = 8.4, 2.4 Hz, 1H), 7.39 – 7.34 (m, 3H), 7.27 (dd, J = 5.2, 3.5 Hz, 2H), 7.25 (s, 1H), 7.02 (d, J = 8.4 Hz, 1H), 5.17 (s, 2H), 4.17 (t, J = 6.5 Hz, 2H), 3.65 (s, 2H), 2.43 (t, J = 7.0 Hz, 2H), 1.86 – 1.79 (m, 2H), 1.69 – 1.62 (m, 2H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 190.95, 171.59, 160.60, 140.58, 136.47, 135.70, 132.89, 132.59, 131.68, 129.63, 129.39, 128.33, 128.02, 127.93, 127.73, 125.26, 123.94, 121.18, 89.58, 81.24, 73.77, 64.72, 40.42, 27.92, 25.31, 19.18; image data were not transcribed
HRMS (ESI⁺) m/z: [M+Na]⁺ calcd for C₂₈H₂₄NaO₄ 447.1572, found 447.1569
SI, pp. S98–S99, S299
(1E,2E)-N1,N2-Bis(2,6-diisopropylphenyl)ethane-1,2-diimine
¹H NMR (500 MHz, CDCl₃) δ 8.12 (s, 2H), 7.22 – 7.19 (m, 4H), 7.19 – 7.15 (m, 2H), 2.96 (hept, J = 6.9 Hz, 4H), 1.23 (d, J = 6.9 Hz, 24H); image data were not transcribed
SI, pp. S100–S101, S300
1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride (IPr·HCl, LC01·HCl)
¹H NMR (500 MHz, DMSO-d₆) δ 10.36 (t, J = 1.6 Hz, 1H), 8.62 (d, J = 1.5 Hz, 2H), 7.69 (t, J = 7.8 Hz, 2H), 7.53 (d, J = 7.9 Hz, 4H), 2.36 (hept, J = 6.8 Hz, 4H), 1.27 (d, J = 6.8 Hz, 12H), 1.17 (d, J = 6.9 Hz, 12H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 144.78, 131.80, 130.05, 126.19, 124.57, 28.61, 24.09, 23.08; image data were not transcribed
SI, pp. S101, S301
1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr, LC01)
¹H NMR (500 MHz, C₆D₆) δ 7.30 (dd, J = 8.3, 7.2 Hz, 2H), 7.19 (d, J = 7.7 Hz, 4H), 6.62 (s, 2H), 2.97 (hept, J = 6.9 Hz, 4H), 1.29 (d, J = 6.9 Hz, 12H), 1.19 (d, J = 6.9 Hz, 12H); image data were not transcribed
¹³C NMR (126 MHz, C₆D₆) δ 146.32, 139.02, 129.02, 128.35, 123.71, 121.58, 28.81, 24.81, 23.64; image data were not transcribed
SI, pp. S102, S302
(2E,3E)-N2,N3-Bis(2,6-diisopropylphenyl)butane-2,3-diimine
¹H NMR (500 MHz, CDCl₃) δ 7.19 (d, J = 8.1 Hz, 4H), 7.12 (dd, J = 8.5, 6.8 Hz, 2H), 2.74 (hept, J = 6.9 Hz, 4H), 2.09 (s, 6H), 1.21 (dd, J = 10.7, 6.9 Hz, 24H); image data were not transcribed
SI, pp. S103, S303
1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium chloride (IPrMe·HCl, LC05·HCl)
¹H NMR (500 MHz, DMSO-d₆) δ 10.05 (s, 1H), 7.69 (t, J = 7.8 Hz, 2H), 7.55 (d, J = 8.0 Hz, 4H), 2.36 – 2.26 (m, 4H), 2.08 (s, 6H), 1.27 – 1.20 (m, 12H), 1.18 – 1.12 (m, 12H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 145.19, 136.63, 132.03, 128.88, 127.84, 124.93, 28.43, 24.79, 22.59, 8.43; image data were not transcribed
SI, pp. S103–S104, S304
4,5-Dichloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride (IPrCl·HCl, LC06·HCl)
¹H NMR (500 MHz, DMSO-d₆) δ 10.94 (s, 1H), 7.75 (t, J = 7.8 Hz, 2H), 7.59 (d, J = 7.8 Hz, 4H), 2.53 – 2.48 (m, 4H), 1.27 (d, J = 6.6 Hz, 12H), 1.15 (d, J = 6.8 Hz, 12H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 137.80, 130.72, 125.08, 118.76, 117.14, 114.64, 21.19, 15.61, 13.91; image data were not transcribed
SI, pp. S105, S305
4-Iodo-2,6-diisopropylaniline
¹H NMR (500 MHz, CDCl₃) δ 7.31 (s, 2H), 3.75 (s, 2H), 2.87 (hept, J = 6.8 Hz, 2H), 1.27 (d, J = 6.8 Hz, 12H); image data were not transcribed
SI, pp. S106, S306
2,6-Diisopropyl-4-methoxyaniline
¹H NMR (500 MHz, CDCl₃) δ 6.74 (s, 2H), 3.85 (s, 3H), 3.54 (s, 2H), 3.04 (hept, J = 6.8 Hz, 2H), 1.35 (d, J = 7.0 Hz, 12H); image data were not transcribed
SI, pp. S107, S307
1,3-Bis(2,6-diisopropyl-4-methoxyphenyl)-1H-imidazol-3-ium chloride (IPrOMe·HCl, LC07·HCl)
¹H NMR (500 MHz, DMSO-d₆) δ 10.07 (s, 1H), 8.44 (d, J = 1.6 Hz, 2H), 7.00 (s, 4H), 3.87 (s, 6H), 2.31 (hept, J = 6.6 Hz, 4H), 1.24 (d, J = 6.8 Hz, 12H), 1.15 (d, J = 6.9 Hz, 12H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 161.53, 146.56, 140.06, 126.48, 122.91, 109.89, 55.74, 28.85, 23.93, 23.00; image data were not transcribed
SI, pp. S107–S108, S308
2,6-Dibenzhydryl-4-methoxyaniline
¹H NMR (500 MHz, CDCl₃) δ 7.29 – 7.16 (m, 12H), 7.11 – 7.05 (m, 8H), 6.18 (s, 2H), 5.46 (s, 2H), 3.40 (s, 3H), 3.12 (s, 2H); image data were not transcribed
SI, pp. S109, S309
1,3-Bis(2,6-dibenzhydryl-4-methoxyphenyl)-1H-imidazol-3-ium chloride (IPr*OMe·HCl, LC08·HCl)
¹H NMR (500 MHz, CDCl₃) δ 12.88 (s, 1H), 7.27 (s, 2H), 7.25 (s, 13H), 7.19 – 7.10 (m, 17H), 6.85 – 6.77 (m, 8H), 6.46 (s, 4H), 5.40 (s, 2H), 5.30 (s, 4H), 3.50 (s, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 160.90, 142.79, 142.46, 141.84, 130.17, 129.25, 128.78, 128.69, 127.12, 127.05 125.39, 123.58, 115.73, 55.30, 51.65; image data were not transcribed
SI, pp. S110, S310
Di(naphthalen-2-yl)methanol
¹H NMR (500 MHz, CDCl₃) δ 7.95 (s, 2H), 7.87 – 7.78 (m, 6H), 7.52 – 7.45 (m, 6H), 6.16 (d, J = 3.5 Hz, 1H), 2.47 (d, J = 3.6 Hz, 1H); image data were not transcribed
SI, pp. S111, S311
2,6-Bis(di(naphthalen-2-yl)methyl)-4-methoxyaniline
¹H NMR (500 MHz, CDCl₃) δ 7.88 – 7.77 (m, 8H), 7.73 – 7.68 (m, 4H), 7.55 – 7.50 (m, 4H), 7.48 – 7.40 (m, 8H), 7.36 (m, 4H), 6.71 – 6.69 (m, 2H), 6.40 – 6.33 (m, 2H), 3.60 (s, 3H), 3.26 (s, 2H); image data were not transcribed
SI, pp. S112, S312
1-(2,6-Bis(di(naphthalen-2-yl)methyl)-4-methoxyphenyl)-3-(2-(di(naphthalen-2-yl)methyl)-6-((2,3-dihydronaphthalen-2-yl)(naphthalen-2-yl)methyl)-4-methoxyphenyl)-1H-imidazol-3-ium chloride (IPr(2-Naph)OMe·HCl, LC09·HCl)
¹H NMR (500 MHz, DMSO-d₆) δ 8.33 (s, 2H), 7.97 (dd, J = 12.3, 7.8 Hz, 8H), 7.86 – 7.81 (m, 4H), 7.78 – 7.70 (m, 8H), 7.60 (d, J = 8.6 Hz, 4H), 7.52 (q, J = 5.9 Hz, 15H), 7.49 – 7.45 (m, 5H), 7.41 (q, J = 4.7 Hz, 7H), 7.21 (d, J = 8.5 Hz, 4H), 6.59 (s, 4H), 6.31 (d, J = 26.1 Hz, 4H), 5.82 (s, 2H), 3.46 (s, 6H); image data were not transcribed
¹³C NMR (126 MHz, DMSO-d₆) δ 140.14, 133.11, 132.71, 132.15, 132.02, 128.16, 128.06, 127.76, 127.71, 127.62, 127.59, 127.41, 126.35, 126.17, 125.97, 125.93, 125.35, 125.19, 117.40, 110.86, 79.25, 54.94, 50.95; image data were not transcribed
SI, pp. S113–S114, S313
1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazole-2-thione (7a)
¹H NMR (500 MHz, C₆D₆) δ 7.27 – 7.23 (m, 2H), 7.14 (d, J = 7.7 Hz, 4H), 6.18 (s, 2H), 2.92 (p, J = 6.9 Hz, 4H), 1.44 (d, J = 6.9 Hz, 12H), 1.16 (d, J = 7.0 Hz, 12H); image data were not transcribed
¹³C NMR (126 MHz, C₆D₆) δ 168.17, 146.77, 134.51, 129.97, 128.16, 124.10, 118.49, 29.06, 24.00, 23.68; image data were not transcribed
SI, pp. S115, S314
3',4',6'-Tributyl-5'-phenyl-1,1':2',1''-terphenyl (6b)
¹H NMR (500 MHz, CDCl₃) δ 7.40 (t, J = 7.3 Hz, 2H), 7.36 – 7.28 (m, 3H), 7.12 – 6.97 (m, 10H), 2.37 (ddd, J = 16.8, 8.4, 4.7 Hz, 4H), 2.07 – 1.99 (m, 2H), 1.37 (tdd, J = 15.5, 11.9, 7.5 Hz, 4H), 1.16 – 1.02 (m, 6H), 0.69 (dt, J = 18.6, 7.3 Hz, 8H), 0.35 (t, J = 7.3 Hz, 3H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 141.74, 141.69, 141.43, 141.42, 141.36, 139.41, 138.47, 136.72, 136.37, 130.77, 130.66, 130.22, 127.78, 127.04, 127.00, 126.51, 125.69, 125.62, 33.60, 32.98, 31.25, 30.64, 30.40, 23.39, 23.33, 22.84, 13.67, 13.64, 13.22; image data were not transcribed
SI, pp. S116, S315
(E)-2-(Hex-3-en-3-yl)benzo[d]thiazole (5a)
¹H NMR (500 MHz, CDCl₃) δ 7.98 (dt, J = 8.1, 0.9 Hz, 1H), 7.81 (dt, J = 7.9, 1.1 Hz, 1H), 7.42 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H), 7.32 (ddd, J = 8.2, 7.2, 1.2 Hz, 1H), 6.48 (t, J = 7.3 Hz, 1H), 2.73 (q, J = 7.5 Hz, 2H), 2.33 (p, J = 7.5 Hz, 2H), 1.16 (dt, J = 22.4, 7.6 Hz, 6H); image data were not transcribed
¹³C NMR (126 MHz, CDCl₃) δ 170.93, 154.08, 138.21, 136.99, 134.57, 125.93, 124.90, 122.98, 121.33, 22.49, 21.99, 14.09, 13.89; image data were not transcribed